The C–C bond that has greater chances of cleavage out of ethane and 2,2-dimethylpropane should be identified. Concept introduction: At extremely elevated temperature, the C–C bond and C–H undergoes homolytic cleavage. This process generates radicals. Greater will be stability of radicals generated more will be chances of cleavage of the particular bond. Bond dissociation value provides concrete evidence for the stability of radicals. If the energy is low that means stable radicals can be generated by very little energy and vive-versa. The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons to the radical carbon more is the stabilization. On the basis of this tertiary C–H bonds react more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

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Answer 1

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Formula Formula Bond dissociation energy (BDE) is the energy required to break a bond, making it an endothermic process. BDE is calculated for a particular bond and therefore consists of fragments such as radicals since it undergoes homolytic bond cleavage. For the homolysis of a X-Y molecule, the energy of bond dissociation is calculated as the difference in the total enthalpy of formation for the reactants and products. X-Y → X + Y BDE = Δ H f X + Δ H f Y – Δ H f X-Y where, ΔHf is the heat of formation.

Chapter 3.1, Problem 3.3E

(a)

Interpretation Introduction

Interpretation: The C–C bond that has greater chances of cleavage out of ethane and 2,2-dimethylpropane should be identified.

Concept introduction: At extremely elevated temperature, the C–C bond and C–H undergoes homolytic cleavage. This process generates radicals. Greater will be stability of radicals generated more will be chances of cleavage of the particular bond. Bond dissociation value provides concrete evidence for the stability of radicals. If the energy is low that means stable radicals can be generated by very little energy and vive-versa.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons to the radical carbon more is the stabilization. On the basis of this tertiary C–H bonds react more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

(b)

Interpretation Introduction

Interpretation: The preferred product formed from attack of HO⋅ radical on 2-dimethylpropane should be written and explained.

Concept introduction: After the homolytic cleavage radicals may recombine with one another and result in variety of alkanes. For example, in pyrolysis of hexane occurs via homolytic fission of either C1–C2 or C2–C3 or C3–C4 . The radicals generated undergo combinations as illustrated below:

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Chlorination of 2-butanone yields two isomeric products, each having the molecular formula C4H7ClO. (a) What are these two compounds? (b) Write structural formulas for the enol intermediates that lead to each of these compounds. (c) Using curved arrows, show the flow of electrons in the reaction of each of the enols with Cl2.

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Answer 2

Question

Formula Formula Bond dissociation energy (BDE) is the energy required to break a bond, making it an endothermic process. BDE is calculated for a particular bond and therefore consists of fragments such as radicals since it undergoes homolytic bond cleavage. For the homolysis of a X-Y molecule, the energy of bond dissociation is calculated as the difference in the total enthalpy of formation for the reactants and products. X-Y → X + Y BDE = Δ H f X + Δ H f Y – Δ H f X-Y where, ΔHf is the heat of formation.

Chapter 3.1, Problem 3.3E

(a)

Interpretation Introduction

Interpretation: The C–C bond that has greater chances of cleavage out of ethane and 2,2-dimethylpropane should be identified.

Concept introduction: At extremely elevated temperature, the C–C bond and C–H undergoes homolytic cleavage. This process generates radicals. Greater will be stability of radicals generated more will be chances of cleavage of the particular bond. Bond dissociation value provides concrete evidence for the stability of radicals. If the energy is low that means stable radicals can be generated by very little energy and vive-versa.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons to the radical carbon more is the stabilization. On the basis of this tertiary C–H bonds react more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

(b)

Interpretation Introduction

Interpretation: The preferred product formed from attack of HO⋅ radical on 2-dimethylpropane should be written and explained.

Concept introduction: After the homolytic cleavage radicals may recombine with one another and result in variety of alkanes. For example, in pyrolysis of hexane occurs via homolytic fission of either C1–C2 or C2–C3 or C3–C4 . The radicals generated undergo combinations as illustrated below:

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Answer 3

Question

Formula Formula Bond dissociation energy (BDE) is the energy required to break a bond, making it an endothermic process. BDE is calculated for a particular bond and therefore consists of fragments such as radicals since it undergoes homolytic bond cleavage. For the homolysis of a X-Y molecule, the energy of bond dissociation is calculated as the difference in the total enthalpy of formation for the reactants and products. X-Y → X + Y BDE = Δ H f X + Δ H f Y – Δ H f X-Y where, ΔHf is the heat of formation.

Chapter 3.1, Problem 3.3E

(a)

Interpretation Introduction

Interpretation: The C–C bond that has greater chances of cleavage out of ethane and 2,2-dimethylpropane should be identified.

Concept introduction: At extremely elevated temperature, the C–C bond and C–H undergoes homolytic cleavage. This process generates radicals. Greater will be stability of radicals generated more will be chances of cleavage of the particular bond. Bond dissociation value provides concrete evidence for the stability of radicals. If the energy is low that means stable radicals can be generated by very little energy and vive-versa.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons to the radical carbon more is the stabilization. On the basis of this tertiary C–H bonds react more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

(b)

Interpretation Introduction

Interpretation: The preferred product formed from attack of HO⋅ radical on 2-dimethylpropane should be written and explained.

Concept introduction: After the homolytic cleavage radicals may recombine with one another and result in variety of alkanes. For example, in pyrolysis of hexane occurs via homolytic fission of either C1–C2 or C2–C3 or C3–C4 . The radicals generated undergo combinations as illustrated below:

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Answer 4

Question

Formula Formula Bond dissociation energy (BDE) is the energy required to break a bond, making it an endothermic process. BDE is calculated for a particular bond and therefore consists of fragments such as radicals since it undergoes homolytic bond cleavage. For the homolysis of a X-Y molecule, the energy of bond dissociation is calculated as the difference in the total enthalpy of formation for the reactants and products. X-Y → X + Y BDE = Δ H f X + Δ H f Y – Δ H f X-Y where, ΔHf is the heat of formation.

Chapter 3.1, Problem 3.3E

(a)

Interpretation Introduction

Interpretation: The C–C bond that has greater chances of cleavage out of ethane and 2,2-dimethylpropane should be identified.

Concept introduction: At extremely elevated temperature, the C–C bond and C–H undergoes homolytic cleavage. This process generates radicals. Greater will be stability of radicals generated more will be chances of cleavage of the particular bond. Bond dissociation value provides concrete evidence for the stability of radicals. If the energy is low that means stable radicals can be generated by very little energy and vive-versa.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons to the radical carbon more is the stabilization. On the basis of this tertiary C–H bonds react more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

(b)

Interpretation Introduction

Interpretation: The preferred product formed from attack of HO⋅ radical on 2-dimethylpropane should be written and explained.

Concept introduction: After the homolytic cleavage radicals may recombine with one another and result in variety of alkanes. For example, in pyrolysis of hexane occurs via homolytic fission of either C1–C2 or C2–C3 or C3–C4 . The radicals generated undergo combinations as illustrated below:

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Answer 5

Chapter 3.1, Problem 3.3E

(a)

Interpretation Introduction

Interpretation: The C–C bond that has greater chances of cleavage out of ethane and 2,2-dimethylpropane should be identified.

Concept introduction: At extremely elevated temperature, the C–C bond and C–H undergoes homolytic cleavage. This process generates radicals. Greater will be stability of radicals generated more will be chances of cleavage of the particular bond. Bond dissociation value provides concrete evidence for the stability of radicals. If the energy is low that means stable radicals can be generated by very little energy and vive-versa.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons to the radical carbon more is the stabilization. On the basis of this tertiary C–H bonds react more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

(b)

Interpretation Introduction

Interpretation: The preferred product formed from attack of HO⋅ radical on 2-dimethylpropane should be written and explained.

Concept introduction: After the homolytic cleavage radicals may recombine with one another and result in variety of alkanes. For example, in pyrolysis of hexane occurs via homolytic fission of either C1–C2 or C2–C3 or C3–C4 . The radicals generated undergo combinations as illustrated below:

Answer 6

Chapter 3.1, Problem 3.3E

(a)

Interpretation Introduction

Interpretation: The C–C bond that has greater chances of cleavage out of ethane and 2,2-dimethylpropane should be identified.

Concept introduction: At extremely elevated temperature, the C–C bond and C–H undergoes homolytic cleavage. This process generates radicals. Greater will be stability of radicals generated more will be chances of cleavage of the particular bond. Bond dissociation value provides concrete evidence for the stability of radicals. If the energy is low that means stable radicals can be generated by very little energy and vive-versa.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons to the radical carbon more is the stabilization. On the basis of this tertiary C–H bonds react more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

Answer 7

Chapter 3.1, Problem 3.3E

(a)

Interpretation Introduction

Interpretation: The C–C bond that has greater chances of cleavage out of ethane and 2,2-dimethylpropane should be identified.

Concept introduction: At extremely elevated temperature, the C–C bond and C–H undergoes homolytic cleavage. This process generates radicals. Greater will be stability of radicals generated more will be chances of cleavage of the particular bond. Bond dissociation value provides concrete evidence for the stability of radicals. If the energy is low that means stable radicals can be generated by very little energy and vive-versa.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons to the radical carbon more is the stabilization. On the basis of this tertiary C–H bonds react more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

Answer 8

(b)

Interpretation Introduction

Interpretation: The preferred product formed from attack of HO⋅ radical on 2-dimethylpropane should be written and explained.

Concept introduction: After the homolytic cleavage radicals may recombine with one another and result in variety of alkanes. For example, in pyrolysis of hexane occurs via homolytic fission of either C1–C2 or C2–C3 or C3–C4 . The radicals generated undergo combinations as illustrated below:

Answer 9

(b)

Interpretation Introduction

Interpretation: The preferred product formed from attack of HO⋅ radical on 2-dimethylpropane should be written and explained.

Concept introduction: After the homolytic cleavage radicals may recombine with one another and result in variety of alkanes. For example, in pyrolysis of hexane occurs via homolytic fission of either C1–C2 or C2–C3 or C3–C4 . The radicals generated undergo combinations as illustrated below:

Answer 10

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Answer 11

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Answer 13

Ch. 3.1 - Prob. 3.2TIY Ch. 3.1 - Prob. 3.3E Ch. 3.4 - Prob. 3.5TIY Ch. 3.5 - Prob. 3.6E Ch. 3.7 - Prob. 3.7E Ch. 3.7 - Prob. 3.9TIY Ch. 3.9 - Prob. 3.11TIY Ch. 3.11 - Prob. 3.12E Ch. 3 - Prob. 15P Ch. 3 - Prob. 16P

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