Numbers of possible stereoisomeric products formed in the monobromination of racemic trans-1,2-dimethylcyclohexane should be determined. Concept introduction: Halogenation products are governed by the achirality or already present stereocenter in the molecule. If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive. If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Question

Want to see the full answer?

Answer 1

Question

Chapter 5, Problem 62P

(a)

Interpretation Introduction

Interpretation:Numbers of possible stereoisomeric products formed in the monobromination of racemic trans-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the monobromination of racemic (R,R)-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(c)

Interpretation Introduction

Interpretation:Whether the various stereoisomeric products obtained from monobromination of racemic trans-1,2-dimethylcyclohexane and (R,R)-1,2-dimethylcyclohexane cannot be separated on the basis of physical properties or not should be indicated.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

What two stereoisomeric alkanes are formed in the catalytic hydrogenation of (Z)-3-methyl-2-hexene? Draw and label the alkanes. In this reaction, what are the relative amounts of each of the two alkanes generated?

(1) Predict the outcome of the addition of HBr to (a) trans-2-pentene, (b) 2-methyl-2-butene, and (c) 4-methylcyclohexene. How many isomers can be formed in each case? (2) Addition of HBr to 3,3-dimethyl-1-butene gives a mixture of two isomeric alkyl bromide products. Draw structures for the two products, and give a mechanistic explanation for their formation.

3-Chloro-2-methylpropene reacts with sodium methoxide in methanol to form 3-methoxy-2-methylpropene. For each of the following changes in the reaction conditions, state whether the reaction rate would increase, decrease, or remain the same. Explain your reasoning. In some cases the identity of the major organic product would be expected to change; in such cases, give the expected major product. (a) the same quantities of reagents are dissolved in half the volume of methanol (b) 3-bromo-2-methylpropene is used in place of 3-chloro-2-methylpropene (c) sodium methanethiolate (CH3SNa) is used in place of of sodium methoxide

Answer 2

Question

Chapter 5, Problem 62P

(a)

Interpretation Introduction

Interpretation:Numbers of possible stereoisomeric products formed in the monobromination of racemic trans-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the monobromination of racemic (R,R)-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(c)

Interpretation Introduction

Interpretation:Whether the various stereoisomeric products obtained from monobromination of racemic trans-1,2-dimethylcyclohexane and (R,R)-1,2-dimethylcyclohexane cannot be separated on the basis of physical properties or not should be indicated.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 5, Problem 62P

(a)

Interpretation Introduction

Interpretation:Numbers of possible stereoisomeric products formed in the monobromination of racemic trans-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the monobromination of racemic (R,R)-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(c)

Interpretation Introduction

Interpretation:Whether the various stereoisomeric products obtained from monobromination of racemic trans-1,2-dimethylcyclohexane and (R,R)-1,2-dimethylcyclohexane cannot be separated on the basis of physical properties or not should be indicated.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 5, Problem 62P

(a)

Interpretation Introduction

Interpretation:Numbers of possible stereoisomeric products formed in the monobromination of racemic trans-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the monobromination of racemic (R,R)-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(c)

Interpretation Introduction

Interpretation:Whether the various stereoisomeric products obtained from monobromination of racemic trans-1,2-dimethylcyclohexane and (R,R)-1,2-dimethylcyclohexane cannot be separated on the basis of physical properties or not should be indicated.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 5, Problem 62P

(a)

Interpretation Introduction

Interpretation:Numbers of possible stereoisomeric products formed in the monobromination of racemic trans-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the monobromination of racemic (R,R)-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(c)

Interpretation Introduction

Interpretation:Whether the various stereoisomeric products obtained from monobromination of racemic trans-1,2-dimethylcyclohexane and (R,R)-1,2-dimethylcyclohexane cannot be separated on the basis of physical properties or not should be indicated.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 6

Chapter 5, Problem 62P

(a)

Interpretation Introduction

Interpretation:Numbers of possible stereoisomeric products formed in the monobromination of racemic trans-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 7

Chapter 5, Problem 62P

(a)

Interpretation Introduction

Interpretation:Numbers of possible stereoisomeric products formed in the monobromination of racemic trans-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 8

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the monobromination of racemic (R,R)-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 9

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the monobromination of racemic (R,R)-1,2-dimethylcyclohexane should be determined.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 10

(c)

Interpretation Introduction

Interpretation:Whether the various stereoisomeric products obtained from monobromination of racemic trans-1,2-dimethylcyclohexane and (R,R)-1,2-dimethylcyclohexane cannot be separated on the basis of physical properties or not should be indicated.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 11

(c)

Interpretation Introduction

Interpretation:Whether the various stereoisomeric products obtained from monobromination of racemic trans-1,2-dimethylcyclohexane and (R,R)-1,2-dimethylcyclohexane cannot be separated on the basis of physical properties or not should be indicated.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 12

Expert Solution & Answer

Answer 13

Expert Solution & Answer

Answer 14

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 15

Ch. 5.1 - Prob. 5.3E Ch. 5.1 - Prob. 5.4E Ch. 5.1 - Prob. 5.5E Ch. 5.2 - Prob. 5.6E Ch. 5.2 - Prob. 5.8TIY Ch. 5.3 - Prob. 5.9E Ch. 5.3 - Prob. 5.11TIY Ch. 5.3 - Prob. 5.12E Ch. 5.4 - Prob. 5.13E Ch. 5.4 - Prob. 5.14E

Solution Summary: The author explains that halogenation products are governed by achirality or already present stereocenter in the molecule.

Want to see the full answer?

Chapter 5 Solutions