(a) Interpretation: The product of the given reaction is to be predicted. Concept introduction: Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo S N 2 reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( RO − ). The mechanism for epoxides under neutral or basic conditions consists of an S N 2 step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of C − O bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the C − O bond.

Question

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Answer 1

Question

Chapter 10, Problem 10.53P

Interpretation Introduction

(a)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 1

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 2

When the given epoxide is treated with sodium azide (basic conditions), the azide ion in sodium azide acts as a nucleophile and attacks the less substituted carbon atom (highlighted in red) of the epoxide. Due to this, the highly strained epoxide ring opens and the azide gets attached to the less substituted carbon atom. In the presence of a solvent such as water, the negatively charged oxygen atom is protonated resulting in the final product. The product of the reaction when the given epoxide is treated with sodium azide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 3

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks at the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 4

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 5

The given reaction conditions are basic as the potassium cyanide is a weak base and nucleophile.

When the given epoxide is treated with potassium cyanide (neutral conditions), the cyanide ion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the cyanide ion gets attached to the carbon. In the presence of a solvent such as ethanediol, the negatively charged oxygen atom is protonated resulting in the final product. The product of the reaction when the given epoxide is treated with sodium azide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 6

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(c)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 7

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 8

The given reaction conditions are acidic as hydrogen cyanide is a weak acid.

When the given epoxide is treated with hydrogen cyanide (acidic conditions), the first step is the protonation of the epoxide oxygen atom. Due to this, a partial positive charge is generated on both carbon atoms in the epoxide. Out of the two carbon atoms, the one that is most substituted would be able to stabilize the partially developed charge, and thus, in the second step, the nucleophile, cyanide ion attacks the most substituted carbon atom from the side opposite to the $C−O$ bond. This is the ring opening step. In the last step, the acid, $HCN$ protonates the negatively charged oxygen atom to yield the final product. The product of the reaction when the given epoxide is treated with hydrogen cyanide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 9

Conclusion

Epoxides can undergo nucleophilic substitution reactions under acidic conditions in which the nucleophile attacks the most substituted carbon atom in the epoxide.

Interpretation Introduction

(d)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 10

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 11

The given reaction conditions are basic as lithium aluminum hydride is a strong base.

$LiAlH4$ is a hydride nucleophile and can open the epoxide ring via an $SN2$ reaction. The H- generated from $LiAlH4$ attacks the least substituted carbon atom in the epoxide. In the next proton transfer step, $H3O+$ , which is a strong acid, protonates the negatively charged oxygen in the epoxide to yield the final product. The product of the reaction when the given epoxide is treated with $LiAlH4$ is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 12

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(e)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

Under acidic conditions, the first step is the protonation the $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 13

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 14

The given reaction conditions are methanol in sulfuric acid. Sulfuric acid is a strong acid. When it is treated with methanol, it will produce protonated methanol which is a strongest known acid. When the given epoxide is treated with protonated methanol, (highly acidic conditions), the first step is the protonation of the oxygen atom in the epoxide. Due to this, a partial positive charge is generated on both the carbon atoms in the epoxide. Out of the two carbon atoms, the one that is most substituted would be able to stabilize the partially developed positive charge. Thus, in the second step, the nucleophile, methoxide ion attacks the most substituted carbon atom from the side opposite to the protonated $C−O$ bond. This is the ring opening step. In the last step, the acid, sulfuric acid protonates the negatively charged oxygen atom to yield the final product. The product of the reaction when the given epoxide is treated with methanol in sulfuric acid is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 15

Conclusion

Epoxides can undergo nucleophilic substitution reactions under acidic conditions in which the nucleophile attacks on the most substituted carbon atom in the epoxide.

Interpretation Introduction

(f)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 16

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 17

When the given epoxide is treated with sodium methoxide in methanol (basic conditions), the methoxide ion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the methoxide ion gets attached to the least substituted carbon atom. The product of the reaction when the given epoxide is treated with sodium methoxide in methanol is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 18

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(g)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 19

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 20

When the given epoxide is treated with benzyl amine in methanol (basic conditions), the nitrogen atom in benzyl amine acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the nitrogen atom gets attached to the least substituted carbon atom. The product of the reaction when the given epoxide is treated with benzyl amine in methanol is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 21

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks on the least substituted carbon atom in the epoxide.

Interpretation Introduction

(h)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of the $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 22

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 23

Methyl lithium is an inorganic methylating agent. When the given epoxide is treated with methyl lithium (basic conditions), the methyl anion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens. In the second step, acidic workup is important so as to protonate the negatively charged oxygen atom.

The product of the reaction when the given epoxide is treated with methyl lithium in the acidic workup is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 24

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

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Answer 2

Question

Chapter 10, Problem 10.53P

Interpretation Introduction

(a)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 1

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 2

When the given epoxide is treated with sodium azide (basic conditions), the azide ion in sodium azide acts as a nucleophile and attacks the less substituted carbon atom (highlighted in red) of the epoxide. Due to this, the highly strained epoxide ring opens and the azide gets attached to the less substituted carbon atom. In the presence of a solvent such as water, the negatively charged oxygen atom is protonated resulting in the final product. The product of the reaction when the given epoxide is treated with sodium azide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 3

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks at the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 4

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 5

The given reaction conditions are basic as the potassium cyanide is a weak base and nucleophile.

When the given epoxide is treated with potassium cyanide (neutral conditions), the cyanide ion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the cyanide ion gets attached to the carbon. In the presence of a solvent such as ethanediol, the negatively charged oxygen atom is protonated resulting in the final product. The product of the reaction when the given epoxide is treated with sodium azide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 6

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(c)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 7

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 8

The given reaction conditions are acidic as hydrogen cyanide is a weak acid.

When the given epoxide is treated with hydrogen cyanide (acidic conditions), the first step is the protonation of the epoxide oxygen atom. Due to this, a partial positive charge is generated on both carbon atoms in the epoxide. Out of the two carbon atoms, the one that is most substituted would be able to stabilize the partially developed charge, and thus, in the second step, the nucleophile, cyanide ion attacks the most substituted carbon atom from the side opposite to the $C−O$ bond. This is the ring opening step. In the last step, the acid, $HCN$ protonates the negatively charged oxygen atom to yield the final product. The product of the reaction when the given epoxide is treated with hydrogen cyanide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 9

Conclusion

Epoxides can undergo nucleophilic substitution reactions under acidic conditions in which the nucleophile attacks the most substituted carbon atom in the epoxide.

Interpretation Introduction

(d)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 10

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 11

The given reaction conditions are basic as lithium aluminum hydride is a strong base.

$LiAlH4$ is a hydride nucleophile and can open the epoxide ring via an $SN2$ reaction. The H- generated from $LiAlH4$ attacks the least substituted carbon atom in the epoxide. In the next proton transfer step, $H3O+$ , which is a strong acid, protonates the negatively charged oxygen in the epoxide to yield the final product. The product of the reaction when the given epoxide is treated with $LiAlH4$ is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 12

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(e)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

Under acidic conditions, the first step is the protonation the $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 13

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 14

The given reaction conditions are methanol in sulfuric acid. Sulfuric acid is a strong acid. When it is treated with methanol, it will produce protonated methanol which is a strongest known acid. When the given epoxide is treated with protonated methanol, (highly acidic conditions), the first step is the protonation of the oxygen atom in the epoxide. Due to this, a partial positive charge is generated on both the carbon atoms in the epoxide. Out of the two carbon atoms, the one that is most substituted would be able to stabilize the partially developed positive charge. Thus, in the second step, the nucleophile, methoxide ion attacks the most substituted carbon atom from the side opposite to the protonated $C−O$ bond. This is the ring opening step. In the last step, the acid, sulfuric acid protonates the negatively charged oxygen atom to yield the final product. The product of the reaction when the given epoxide is treated with methanol in sulfuric acid is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 15

Conclusion

Epoxides can undergo nucleophilic substitution reactions under acidic conditions in which the nucleophile attacks on the most substituted carbon atom in the epoxide.

Interpretation Introduction

(f)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 16

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 17

When the given epoxide is treated with sodium methoxide in methanol (basic conditions), the methoxide ion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the methoxide ion gets attached to the least substituted carbon atom. The product of the reaction when the given epoxide is treated with sodium methoxide in methanol is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 18

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(g)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 19

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 20

When the given epoxide is treated with benzyl amine in methanol (basic conditions), the nitrogen atom in benzyl amine acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the nitrogen atom gets attached to the least substituted carbon atom. The product of the reaction when the given epoxide is treated with benzyl amine in methanol is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 21

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks on the least substituted carbon atom in the epoxide.

Interpretation Introduction

(h)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of the $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 22

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 23

Methyl lithium is an inorganic methylating agent. When the given epoxide is treated with methyl lithium (basic conditions), the methyl anion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens. In the second step, acidic workup is important so as to protonate the negatively charged oxygen atom.

The product of the reaction when the given epoxide is treated with methyl lithium in the acidic workup is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 24

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

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Answer 3

Question

Chapter 10, Problem 10.53P

Interpretation Introduction

(a)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 1

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 2

When the given epoxide is treated with sodium azide (basic conditions), the azide ion in sodium azide acts as a nucleophile and attacks the less substituted carbon atom (highlighted in red) of the epoxide. Due to this, the highly strained epoxide ring opens and the azide gets attached to the less substituted carbon atom. In the presence of a solvent such as water, the negatively charged oxygen atom is protonated resulting in the final product. The product of the reaction when the given epoxide is treated with sodium azide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 3

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks at the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 4

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 5

The given reaction conditions are basic as the potassium cyanide is a weak base and nucleophile.

When the given epoxide is treated with potassium cyanide (neutral conditions), the cyanide ion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the cyanide ion gets attached to the carbon. In the presence of a solvent such as ethanediol, the negatively charged oxygen atom is protonated resulting in the final product. The product of the reaction when the given epoxide is treated with sodium azide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 6

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(c)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 7

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 8

The given reaction conditions are acidic as hydrogen cyanide is a weak acid.

When the given epoxide is treated with hydrogen cyanide (acidic conditions), the first step is the protonation of the epoxide oxygen atom. Due to this, a partial positive charge is generated on both carbon atoms in the epoxide. Out of the two carbon atoms, the one that is most substituted would be able to stabilize the partially developed charge, and thus, in the second step, the nucleophile, cyanide ion attacks the most substituted carbon atom from the side opposite to the $C−O$ bond. This is the ring opening step. In the last step, the acid, $HCN$ protonates the negatively charged oxygen atom to yield the final product. The product of the reaction when the given epoxide is treated with hydrogen cyanide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 9

Conclusion

Epoxides can undergo nucleophilic substitution reactions under acidic conditions in which the nucleophile attacks the most substituted carbon atom in the epoxide.

Interpretation Introduction

(d)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 10

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 11

The given reaction conditions are basic as lithium aluminum hydride is a strong base.

$LiAlH4$ is a hydride nucleophile and can open the epoxide ring via an $SN2$ reaction. The H- generated from $LiAlH4$ attacks the least substituted carbon atom in the epoxide. In the next proton transfer step, $H3O+$ , which is a strong acid, protonates the negatively charged oxygen in the epoxide to yield the final product. The product of the reaction when the given epoxide is treated with $LiAlH4$ is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 12

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(e)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

Under acidic conditions, the first step is the protonation the $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 13

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 14

The given reaction conditions are methanol in sulfuric acid. Sulfuric acid is a strong acid. When it is treated with methanol, it will produce protonated methanol which is a strongest known acid. When the given epoxide is treated with protonated methanol, (highly acidic conditions), the first step is the protonation of the oxygen atom in the epoxide. Due to this, a partial positive charge is generated on both the carbon atoms in the epoxide. Out of the two carbon atoms, the one that is most substituted would be able to stabilize the partially developed positive charge. Thus, in the second step, the nucleophile, methoxide ion attacks the most substituted carbon atom from the side opposite to the protonated $C−O$ bond. This is the ring opening step. In the last step, the acid, sulfuric acid protonates the negatively charged oxygen atom to yield the final product. The product of the reaction when the given epoxide is treated with methanol in sulfuric acid is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 15

Conclusion

Epoxides can undergo nucleophilic substitution reactions under acidic conditions in which the nucleophile attacks on the most substituted carbon atom in the epoxide.

Interpretation Introduction

(f)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 16

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 17

When the given epoxide is treated with sodium methoxide in methanol (basic conditions), the methoxide ion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the methoxide ion gets attached to the least substituted carbon atom. The product of the reaction when the given epoxide is treated with sodium methoxide in methanol is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 18

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(g)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 19

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 20

When the given epoxide is treated with benzyl amine in methanol (basic conditions), the nitrogen atom in benzyl amine acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the nitrogen atom gets attached to the least substituted carbon atom. The product of the reaction when the given epoxide is treated with benzyl amine in methanol is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 21

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks on the least substituted carbon atom in the epoxide.

Interpretation Introduction

(h)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of the $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 22

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 23

Methyl lithium is an inorganic methylating agent. When the given epoxide is treated with methyl lithium (basic conditions), the methyl anion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens. In the second step, acidic workup is important so as to protonate the negatively charged oxygen atom.

The product of the reaction when the given epoxide is treated with methyl lithium in the acidic workup is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 24

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

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Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 4

Question

Chapter 10, Problem 10.53P

Interpretation Introduction

(a)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 1

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 2

When the given epoxide is treated with sodium azide (basic conditions), the azide ion in sodium azide acts as a nucleophile and attacks the less substituted carbon atom (highlighted in red) of the epoxide. Due to this, the highly strained epoxide ring opens and the azide gets attached to the less substituted carbon atom. In the presence of a solvent such as water, the negatively charged oxygen atom is protonated resulting in the final product. The product of the reaction when the given epoxide is treated with sodium azide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 3

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks at the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 4

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 5

The given reaction conditions are basic as the potassium cyanide is a weak base and nucleophile.

When the given epoxide is treated with potassium cyanide (neutral conditions), the cyanide ion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the cyanide ion gets attached to the carbon. In the presence of a solvent such as ethanediol, the negatively charged oxygen atom is protonated resulting in the final product. The product of the reaction when the given epoxide is treated with sodium azide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 6

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(c)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 7

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 8

The given reaction conditions are acidic as hydrogen cyanide is a weak acid.

When the given epoxide is treated with hydrogen cyanide (acidic conditions), the first step is the protonation of the epoxide oxygen atom. Due to this, a partial positive charge is generated on both carbon atoms in the epoxide. Out of the two carbon atoms, the one that is most substituted would be able to stabilize the partially developed charge, and thus, in the second step, the nucleophile, cyanide ion attacks the most substituted carbon atom from the side opposite to the $C−O$ bond. This is the ring opening step. In the last step, the acid, $HCN$ protonates the negatively charged oxygen atom to yield the final product. The product of the reaction when the given epoxide is treated with hydrogen cyanide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 9

Conclusion

Epoxides can undergo nucleophilic substitution reactions under acidic conditions in which the nucleophile attacks the most substituted carbon atom in the epoxide.

Interpretation Introduction

(d)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 10

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 11

The given reaction conditions are basic as lithium aluminum hydride is a strong base.

$LiAlH4$ is a hydride nucleophile and can open the epoxide ring via an $SN2$ reaction. The H- generated from $LiAlH4$ attacks the least substituted carbon atom in the epoxide. In the next proton transfer step, $H3O+$ , which is a strong acid, protonates the negatively charged oxygen in the epoxide to yield the final product. The product of the reaction when the given epoxide is treated with $LiAlH4$ is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 12

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(e)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

Under acidic conditions, the first step is the protonation the $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 13

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 14

The given reaction conditions are methanol in sulfuric acid. Sulfuric acid is a strong acid. When it is treated with methanol, it will produce protonated methanol which is a strongest known acid. When the given epoxide is treated with protonated methanol, (highly acidic conditions), the first step is the protonation of the oxygen atom in the epoxide. Due to this, a partial positive charge is generated on both the carbon atoms in the epoxide. Out of the two carbon atoms, the one that is most substituted would be able to stabilize the partially developed positive charge. Thus, in the second step, the nucleophile, methoxide ion attacks the most substituted carbon atom from the side opposite to the protonated $C−O$ bond. This is the ring opening step. In the last step, the acid, sulfuric acid protonates the negatively charged oxygen atom to yield the final product. The product of the reaction when the given epoxide is treated with methanol in sulfuric acid is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 15

Conclusion

Epoxides can undergo nucleophilic substitution reactions under acidic conditions in which the nucleophile attacks on the most substituted carbon atom in the epoxide.

Interpretation Introduction

(f)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 16

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 17

When the given epoxide is treated with sodium methoxide in methanol (basic conditions), the methoxide ion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the methoxide ion gets attached to the least substituted carbon atom. The product of the reaction when the given epoxide is treated with sodium methoxide in methanol is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 18

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(g)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 19

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 20

When the given epoxide is treated with benzyl amine in methanol (basic conditions), the nitrogen atom in benzyl amine acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the nitrogen atom gets attached to the least substituted carbon atom. The product of the reaction when the given epoxide is treated with benzyl amine in methanol is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 21

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks on the least substituted carbon atom in the epoxide.

Interpretation Introduction

(h)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of the $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 22

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 23

Methyl lithium is an inorganic methylating agent. When the given epoxide is treated with methyl lithium (basic conditions), the methyl anion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens. In the second step, acidic workup is important so as to protonate the negatively charged oxygen atom.

The product of the reaction when the given epoxide is treated with methyl lithium in the acidic workup is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 24

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

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Answer 5

Chapter 10, Problem 10.53P

Interpretation Introduction

(a)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 1

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 2

When the given epoxide is treated with sodium azide (basic conditions), the azide ion in sodium azide acts as a nucleophile and attacks the less substituted carbon atom (highlighted in red) of the epoxide. Due to this, the highly strained epoxide ring opens and the azide gets attached to the less substituted carbon atom. In the presence of a solvent such as water, the negatively charged oxygen atom is protonated resulting in the final product. The product of the reaction when the given epoxide is treated with sodium azide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 3

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks at the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 4

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 5

The given reaction conditions are basic as the potassium cyanide is a weak base and nucleophile.

When the given epoxide is treated with potassium cyanide (neutral conditions), the cyanide ion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the cyanide ion gets attached to the carbon. In the presence of a solvent such as ethanediol, the negatively charged oxygen atom is protonated resulting in the final product. The product of the reaction when the given epoxide is treated with sodium azide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 6

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(c)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 7

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 8

The given reaction conditions are acidic as hydrogen cyanide is a weak acid.

When the given epoxide is treated with hydrogen cyanide (acidic conditions), the first step is the protonation of the epoxide oxygen atom. Due to this, a partial positive charge is generated on both carbon atoms in the epoxide. Out of the two carbon atoms, the one that is most substituted would be able to stabilize the partially developed charge, and thus, in the second step, the nucleophile, cyanide ion attacks the most substituted carbon atom from the side opposite to the $C−O$ bond. This is the ring opening step. In the last step, the acid, $HCN$ protonates the negatively charged oxygen atom to yield the final product. The product of the reaction when the given epoxide is treated with hydrogen cyanide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 9

Conclusion

Epoxides can undergo nucleophilic substitution reactions under acidic conditions in which the nucleophile attacks the most substituted carbon atom in the epoxide.

Interpretation Introduction

(d)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 10

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 11

The given reaction conditions are basic as lithium aluminum hydride is a strong base.

$LiAlH4$ is a hydride nucleophile and can open the epoxide ring via an $SN2$ reaction. The H- generated from $LiAlH4$ attacks the least substituted carbon atom in the epoxide. In the next proton transfer step, $H3O+$ , which is a strong acid, protonates the negatively charged oxygen in the epoxide to yield the final product. The product of the reaction when the given epoxide is treated with $LiAlH4$ is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 12

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(e)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

Under acidic conditions, the first step is the protonation the $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 13

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 14

The given reaction conditions are methanol in sulfuric acid. Sulfuric acid is a strong acid. When it is treated with methanol, it will produce protonated methanol which is a strongest known acid. When the given epoxide is treated with protonated methanol, (highly acidic conditions), the first step is the protonation of the oxygen atom in the epoxide. Due to this, a partial positive charge is generated on both the carbon atoms in the epoxide. Out of the two carbon atoms, the one that is most substituted would be able to stabilize the partially developed positive charge. Thus, in the second step, the nucleophile, methoxide ion attacks the most substituted carbon atom from the side opposite to the protonated $C−O$ bond. This is the ring opening step. In the last step, the acid, sulfuric acid protonates the negatively charged oxygen atom to yield the final product. The product of the reaction when the given epoxide is treated with methanol in sulfuric acid is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 15

Conclusion

Epoxides can undergo nucleophilic substitution reactions under acidic conditions in which the nucleophile attacks on the most substituted carbon atom in the epoxide.

Interpretation Introduction

(f)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 16

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 17

When the given epoxide is treated with sodium methoxide in methanol (basic conditions), the methoxide ion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the methoxide ion gets attached to the least substituted carbon atom. The product of the reaction when the given epoxide is treated with sodium methoxide in methanol is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 18

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Interpretation Introduction

(g)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 19

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 20

When the given epoxide is treated with benzyl amine in methanol (basic conditions), the nitrogen atom in benzyl amine acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the nitrogen atom gets attached to the least substituted carbon atom. The product of the reaction when the given epoxide is treated with benzyl amine in methanol is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 21

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks on the least substituted carbon atom in the epoxide.

Interpretation Introduction

(h)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of the $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 22

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 23

Methyl lithium is an inorganic methylating agent. When the given epoxide is treated with methyl lithium (basic conditions), the methyl anion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens. In the second step, acidic workup is important so as to protonate the negatively charged oxygen atom.

The product of the reaction when the given epoxide is treated with methyl lithium in the acidic workup is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 24

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Answer 6

Chapter 10, Problem 10.53P

Interpretation Introduction

(a)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 1

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 2

When the given epoxide is treated with sodium azide (basic conditions), the azide ion in sodium azide acts as a nucleophile and attacks the less substituted carbon atom (highlighted in red) of the epoxide. Due to this, the highly strained epoxide ring opens and the azide gets attached to the less substituted carbon atom. In the presence of a solvent such as water, the negatively charged oxygen atom is protonated resulting in the final product. The product of the reaction when the given epoxide is treated with sodium azide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 3

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Answer 7

Chapter 10, Problem 10.53P

Interpretation Introduction

(a)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Answer 8

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 1

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 2

When the given epoxide is treated with sodium azide (basic conditions), the azide ion in sodium azide acts as a nucleophile and attacks the less substituted carbon atom (highlighted in red) of the epoxide. Due to this, the highly strained epoxide ring opens and the azide gets attached to the less substituted carbon atom. In the presence of a solvent such as water, the negatively charged oxygen atom is protonated resulting in the final product. The product of the reaction when the given epoxide is treated with sodium azide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 3

Answer 13

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Answer 14

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks at the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 4

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 5

The given reaction conditions are basic as the potassium cyanide is a weak base and nucleophile.

When the given epoxide is treated with potassium cyanide (neutral conditions), the cyanide ion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the cyanide ion gets attached to the carbon. In the presence of a solvent such as ethanediol, the negatively charged oxygen atom is protonated resulting in the final product. The product of the reaction when the given epoxide is treated with sodium azide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 6

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Answer 15

Interpretation Introduction

(b)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks at the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Answer 16

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 4

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 5

The given reaction conditions are basic as the potassium cyanide is a weak base and nucleophile.

When the given epoxide is treated with potassium cyanide (neutral conditions), the cyanide ion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the cyanide ion gets attached to the carbon. In the presence of a solvent such as ethanediol, the negatively charged oxygen atom is protonated resulting in the final product. The product of the reaction when the given epoxide is treated with sodium azide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 6

Answer 21

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Answer 22

Interpretation Introduction

(c)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 7

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 8

The given reaction conditions are acidic as hydrogen cyanide is a weak acid.

When the given epoxide is treated with hydrogen cyanide (acidic conditions), the first step is the protonation of the epoxide oxygen atom. Due to this, a partial positive charge is generated on both carbon atoms in the epoxide. Out of the two carbon atoms, the one that is most substituted would be able to stabilize the partially developed charge, and thus, in the second step, the nucleophile, cyanide ion attacks the most substituted carbon atom from the side opposite to the $C−O$ bond. This is the ring opening step. In the last step, the acid, $HCN$ protonates the negatively charged oxygen atom to yield the final product. The product of the reaction when the given epoxide is treated with hydrogen cyanide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 9

Conclusion

Epoxides can undergo nucleophilic substitution reactions under acidic conditions in which the nucleophile attacks the most substituted carbon atom in the epoxide.

Answer 23

Interpretation Introduction

(c)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Answer 24

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 7

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 8

The given reaction conditions are acidic as hydrogen cyanide is a weak acid.

When the given epoxide is treated with hydrogen cyanide (acidic conditions), the first step is the protonation of the epoxide oxygen atom. Due to this, a partial positive charge is generated on both carbon atoms in the epoxide. Out of the two carbon atoms, the one that is most substituted would be able to stabilize the partially developed charge, and thus, in the second step, the nucleophile, cyanide ion attacks the most substituted carbon atom from the side opposite to the $C−O$ bond. This is the ring opening step. In the last step, the acid, $HCN$ protonates the negatively charged oxygen atom to yield the final product. The product of the reaction when the given epoxide is treated with hydrogen cyanide is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 9

Answer 29

Conclusion

Epoxides can undergo nucleophilic substitution reactions under acidic conditions in which the nucleophile attacks the most substituted carbon atom in the epoxide.

Answer 30

Interpretation Introduction

(d)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 10

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 11

The given reaction conditions are basic as lithium aluminum hydride is a strong base.

$LiAlH4$ is a hydride nucleophile and can open the epoxide ring via an $SN2$ reaction. The H- generated from $LiAlH4$ attacks the least substituted carbon atom in the epoxide. In the next proton transfer step, $H3O+$ , which is a strong acid, protonates the negatively charged oxygen in the epoxide to yield the final product. The product of the reaction when the given epoxide is treated with $LiAlH4$ is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 12

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Answer 31

Interpretation Introduction

(d)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Answer 32

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 10

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 11

The given reaction conditions are basic as lithium aluminum hydride is a strong base.

$LiAlH4$ is a hydride nucleophile and can open the epoxide ring via an $SN2$ reaction. The H- generated from $LiAlH4$ attacks the least substituted carbon atom in the epoxide. In the next proton transfer step, $H3O+$ , which is a strong acid, protonates the negatively charged oxygen in the epoxide to yield the final product. The product of the reaction when the given epoxide is treated with $LiAlH4$ is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 12

Answer 37

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Answer 38

Interpretation Introduction

(e)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

Under acidic conditions, the first step is the protonation the $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 13

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 14

The given reaction conditions are methanol in sulfuric acid. Sulfuric acid is a strong acid. When it is treated with methanol, it will produce protonated methanol which is a strongest known acid. When the given epoxide is treated with protonated methanol, (highly acidic conditions), the first step is the protonation of the oxygen atom in the epoxide. Due to this, a partial positive charge is generated on both the carbon atoms in the epoxide. Out of the two carbon atoms, the one that is most substituted would be able to stabilize the partially developed positive charge. Thus, in the second step, the nucleophile, methoxide ion attacks the most substituted carbon atom from the side opposite to the protonated $C−O$ bond. This is the ring opening step. In the last step, the acid, sulfuric acid protonates the negatively charged oxygen atom to yield the final product. The product of the reaction when the given epoxide is treated with methanol in sulfuric acid is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 15

Conclusion

Epoxides can undergo nucleophilic substitution reactions under acidic conditions in which the nucleophile attacks on the most substituted carbon atom in the epoxide.

Answer 39

Interpretation Introduction

(e)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

Under acidic conditions, the first step is the protonation the $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Answer 40

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 13

Answer 41

Expert Solution

Answer 42

Expert Solution

Answer 43

Expert Solution

Answer 44

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 14

The given reaction conditions are methanol in sulfuric acid. Sulfuric acid is a strong acid. When it is treated with methanol, it will produce protonated methanol which is a strongest known acid. When the given epoxide is treated with protonated methanol, (highly acidic conditions), the first step is the protonation of the oxygen atom in the epoxide. Due to this, a partial positive charge is generated on both the carbon atoms in the epoxide. Out of the two carbon atoms, the one that is most substituted would be able to stabilize the partially developed positive charge. Thus, in the second step, the nucleophile, methoxide ion attacks the most substituted carbon atom from the side opposite to the protonated $C−O$ bond. This is the ring opening step. In the last step, the acid, sulfuric acid protonates the negatively charged oxygen atom to yield the final product. The product of the reaction when the given epoxide is treated with methanol in sulfuric acid is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 15

Answer 45

Conclusion

Epoxides can undergo nucleophilic substitution reactions under acidic conditions in which the nucleophile attacks on the most substituted carbon atom in the epoxide.

Answer 46

Interpretation Introduction

(f)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 16

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 17

When the given epoxide is treated with sodium methoxide in methanol (basic conditions), the methoxide ion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the methoxide ion gets attached to the least substituted carbon atom. The product of the reaction when the given epoxide is treated with sodium methoxide in methanol is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 18

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Answer 47

Interpretation Introduction

(f)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Answer 48

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 16

Answer 49

Expert Solution

Answer 50

Expert Solution

Answer 51

Expert Solution

Answer 52

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 17

When the given epoxide is treated with sodium methoxide in methanol (basic conditions), the methoxide ion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the methoxide ion gets attached to the least substituted carbon atom. The product of the reaction when the given epoxide is treated with sodium methoxide in methanol is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 18

Answer 53

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Answer 54

Interpretation Introduction

(g)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 19

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 20

When the given epoxide is treated with benzyl amine in methanol (basic conditions), the nitrogen atom in benzyl amine acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the nitrogen atom gets attached to the least substituted carbon atom. The product of the reaction when the given epoxide is treated with benzyl amine in methanol is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 21

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks on the least substituted carbon atom in the epoxide.

Answer 55

Interpretation Introduction

(g)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Answer 56

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 19

Answer 57

Expert Solution

Answer 58

Expert Solution

Answer 59

Expert Solution

Answer 60

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 20

When the given epoxide is treated with benzyl amine in methanol (basic conditions), the nitrogen atom in benzyl amine acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens and the nitrogen atom gets attached to the least substituted carbon atom. The product of the reaction when the given epoxide is treated with benzyl amine in methanol is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 21

Answer 61

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks on the least substituted carbon atom in the epoxide.

Answer 62

Interpretation Introduction

(h)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of the $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 22

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 23

Methyl lithium is an inorganic methylating agent. When the given epoxide is treated with methyl lithium (basic conditions), the methyl anion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens. In the second step, acidic workup is important so as to protonate the negatively charged oxygen atom.

The product of the reaction when the given epoxide is treated with methyl lithium in the acidic workup is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 24

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.

Answer 63

Interpretation Introduction

(h)

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

Epoxides react readily under neutral, basic, or acidic conditions. Epoxides can undergo $SN2$ reactions in neutral or basic reaction conditions so as to relieve the ring strain, and this compensates for the poor leaving group ability of alkoxides ( $RO−$ ).

The mechanism for the epoxides under neutral or basic conditions consists of an $SN2$ step followed by a proton transfer reaction. Under neutral or basic conditions, a nucleophile attacks an epoxide at the least substituted carbon atom (less sterically hindered) of the ring, from the side opposite to the oxygen atom. Under acidic conditions, the first step is the protonation of the $C−O$ bond. This generates a partial positive charge on the carbon atoms in the epoxide. In the second step, a nucleophile attacks the most substituted carbon atom in the epoxide from the side opposite to the $C−O$ bond.

Answer 64

Expert Solution

Answer to Problem 10.53P

The product of the given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 22

Answer 65

Expert Solution

Answer 66

Expert Solution

Answer 67

Expert Solution

Answer 68

Explanation of Solution

The given reaction is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 23

Methyl lithium is an inorganic methylating agent. When the given epoxide is treated with methyl lithium (basic conditions), the methyl anion acts as a nucleophile and attacks the least substituted carbon atom of the epoxide. Due to this, the highly strained epoxide ring opens. In the second step, acidic workup is important so as to protonate the negatively charged oxygen atom.

The product of the reaction when the given epoxide is treated with methyl lithium in the acidic workup is as below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 10, Problem 10.53P , additional homework tip 24

Answer 69

Conclusion

Epoxides can undergo nucleophilic substitution reactions under neutral or basic conditions in which the nucleophile attacks the least substituted carbon atom in the epoxide.