(a) Interpretation: The mechanism of the given radical rearrangement reaction is to be drawn. Concept introduction: In homolysis, the radicals from a breaking of the weakest bond of the molecule give the major products. The weakest bond possesses the smallest bond dissociation energy . The stability order for radicals is methyl radical < 1 o radical < 2 o radical < 3 o radical . Since radicals are electron-poor like carbocation the electron-donating groups increases the stability of radical. In the case of allyl and benzyl radicals the delocalization of the unpaired electron about the entire species. Like carbocation rearrangement radicals also undergo radical rearrangement reaction to form the more stable radical.

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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 25, Problem 25.77P

Interpretation Introduction

(a)

Interpretation:

The mechanism of the given radical rearrangement reaction is to be drawn.

Concept introduction:

In homolysis, the radicals from a breaking of the weakest bond of the molecule give the major products. The weakest bond possesses the smallest bond dissociation energy. The stability order for radicals is methyl radical < 1oradical < 2oradical < 3oradical. Since radicals are electron-poor like carbocation the electron-donating groups increases the stability of radical. In the case of allyl and benzyl radicals the delocalization of the unpaired electron about the entire species. Like carbocation rearrangement radicals also undergo radical rearrangement reaction to form the more stable radical.

Interpretation Introduction

(b)

Interpretation:

What should student conclude regarding the alkyl rearrangement for a given reaction from a 1H NMR spectrum of the product is to be explained.

Concept introduction:

In homolysis, the radicals from a breaking of the weakest bond of the molecule give the major products. The weakest bond possesses the smallest bond dissociation energy. The stability order for radicals is methyl radical < 1oradical < 2oradical < 3oradical. Since radicals are electron-poor like carbocation the electron-donating groups increases the stability of radical. In the case of allyl and benzyl radicals the delocalization of the unpaired electron about the entire species. Like carbocation rearrangement radicals also undergo radical rearrangement reaction to form the more stable radical.

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The reaction: A + B ⇌ 2 C, can be represented by the equilibrium expression, KC =[C]2[A][B]=258 at 520K.When 1.00 M of C was allowed to reach equilibrium and 0.055 M of A was formed. If this reaction wasperformed at the same temperature using 0.500 M C, what would the equilibrium concentration of Abe?

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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 25, Problem 25.77P

Interpretation Introduction

(a)

Interpretation:

The mechanism of the given radical rearrangement reaction is to be drawn.

Concept introduction:

In homolysis, the radicals from a breaking of the weakest bond of the molecule give the major products. The weakest bond possesses the smallest bond dissociation energy. The stability order for radicals is methyl radical < 1oradical < 2oradical < 3oradical. Since radicals are electron-poor like carbocation the electron-donating groups increases the stability of radical. In the case of allyl and benzyl radicals the delocalization of the unpaired electron about the entire species. Like carbocation rearrangement radicals also undergo radical rearrangement reaction to form the more stable radical.

Interpretation Introduction

(b)

Interpretation:

What should student conclude regarding the alkyl rearrangement for a given reaction from a 1H NMR spectrum of the product is to be explained.

Concept introduction:

In homolysis, the radicals from a breaking of the weakest bond of the molecule give the major products. The weakest bond possesses the smallest bond dissociation energy. The stability order for radicals is methyl radical < 1oradical < 2oradical < 3oradical. Since radicals are electron-poor like carbocation the electron-donating groups increases the stability of radical. In the case of allyl and benzyl radicals the delocalization of the unpaired electron about the entire species. Like carbocation rearrangement radicals also undergo radical rearrangement reaction to form the more stable radical.

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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 25, Problem 25.77P

Interpretation Introduction

(a)

Interpretation:

The mechanism of the given radical rearrangement reaction is to be drawn.

Concept introduction:

In homolysis, the radicals from a breaking of the weakest bond of the molecule give the major products. The weakest bond possesses the smallest bond dissociation energy. The stability order for radicals is methyl radical < 1oradical < 2oradical < 3oradical. Since radicals are electron-poor like carbocation the electron-donating groups increases the stability of radical. In the case of allyl and benzyl radicals the delocalization of the unpaired electron about the entire species. Like carbocation rearrangement radicals also undergo radical rearrangement reaction to form the more stable radical.

Interpretation Introduction

(b)

Interpretation:

What should student conclude regarding the alkyl rearrangement for a given reaction from a 1H NMR spectrum of the product is to be explained.

Concept introduction:

In homolysis, the radicals from a breaking of the weakest bond of the molecule give the major products. The weakest bond possesses the smallest bond dissociation energy. The stability order for radicals is methyl radical < 1oradical < 2oradical < 3oradical. Since radicals are electron-poor like carbocation the electron-donating groups increases the stability of radical. In the case of allyl and benzyl radicals the delocalization of the unpaired electron about the entire species. Like carbocation rearrangement radicals also undergo radical rearrangement reaction to form the more stable radical.

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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 25, Problem 25.77P

Interpretation Introduction

(a)

Interpretation:

The mechanism of the given radical rearrangement reaction is to be drawn.

Concept introduction:

In homolysis, the radicals from a breaking of the weakest bond of the molecule give the major products. The weakest bond possesses the smallest bond dissociation energy. The stability order for radicals is methyl radical < 1oradical < 2oradical < 3oradical. Since radicals are electron-poor like carbocation the electron-donating groups increases the stability of radical. In the case of allyl and benzyl radicals the delocalization of the unpaired electron about the entire species. Like carbocation rearrangement radicals also undergo radical rearrangement reaction to form the more stable radical.

Interpretation Introduction

(b)

Interpretation:

What should student conclude regarding the alkyl rearrangement for a given reaction from a 1H NMR spectrum of the product is to be explained.

Concept introduction:

In homolysis, the radicals from a breaking of the weakest bond of the molecule give the major products. The weakest bond possesses the smallest bond dissociation energy. The stability order for radicals is methyl radical < 1oradical < 2oradical < 3oradical. Since radicals are electron-poor like carbocation the electron-donating groups increases the stability of radical. In the case of allyl and benzyl radicals the delocalization of the unpaired electron about the entire species. Like carbocation rearrangement radicals also undergo radical rearrangement reaction to form the more stable radical.

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Answer 5

Chapter 25, Problem 25.77P

Interpretation Introduction

(a)

Interpretation:

The mechanism of the given radical rearrangement reaction is to be drawn.

Concept introduction:

In homolysis, the radicals from a breaking of the weakest bond of the molecule give the major products. The weakest bond possesses the smallest bond dissociation energy. The stability order for radicals is methyl radical < 1oradical < 2oradical < 3oradical. Since radicals are electron-poor like carbocation the electron-donating groups increases the stability of radical. In the case of allyl and benzyl radicals the delocalization of the unpaired electron about the entire species. Like carbocation rearrangement radicals also undergo radical rearrangement reaction to form the more stable radical.

Interpretation Introduction

(b)

Interpretation:

What should student conclude regarding the alkyl rearrangement for a given reaction from a 1H NMR spectrum of the product is to be explained.

Concept introduction:

In homolysis, the radicals from a breaking of the weakest bond of the molecule give the major products. The weakest bond possesses the smallest bond dissociation energy. The stability order for radicals is methyl radical < 1oradical < 2oradical < 3oradical. Since radicals are electron-poor like carbocation the electron-donating groups increases the stability of radical. In the case of allyl and benzyl radicals the delocalization of the unpaired electron about the entire species. Like carbocation rearrangement radicals also undergo radical rearrangement reaction to form the more stable radical.

Answer 6

Chapter 25, Problem 25.77P

Interpretation Introduction

(a)

Interpretation:

The mechanism of the given radical rearrangement reaction is to be drawn.

Concept introduction:

In homolysis, the radicals from a breaking of the weakest bond of the molecule give the major products. The weakest bond possesses the smallest bond dissociation energy. The stability order for radicals is methyl radical < 1oradical < 2oradical < 3oradical. Since radicals are electron-poor like carbocation the electron-donating groups increases the stability of radical. In the case of allyl and benzyl radicals the delocalization of the unpaired electron about the entire species. Like carbocation rearrangement radicals also undergo radical rearrangement reaction to form the more stable radical.

Answer 7

Chapter 25, Problem 25.77P

Interpretation Introduction

(a)

Interpretation:

The mechanism of the given radical rearrangement reaction is to be drawn.

Concept introduction:

In homolysis, the radicals from a breaking of the weakest bond of the molecule give the major products. The weakest bond possesses the smallest bond dissociation energy. The stability order for radicals is methyl radical < 1oradical < 2oradical < 3oradical. Since radicals are electron-poor like carbocation the electron-donating groups increases the stability of radical. In the case of allyl and benzyl radicals the delocalization of the unpaired electron about the entire species. Like carbocation rearrangement radicals also undergo radical rearrangement reaction to form the more stable radical.

Answer 8

Interpretation Introduction

(b)

Interpretation:

What should student conclude regarding the alkyl rearrangement for a given reaction from a 1H NMR spectrum of the product is to be explained.

Concept introduction:

In homolysis, the radicals from a breaking of the weakest bond of the molecule give the major products. The weakest bond possesses the smallest bond dissociation energy. The stability order for radicals is methyl radical < 1oradical < 2oradical < 3oradical. Since radicals are electron-poor like carbocation the electron-donating groups increases the stability of radical. In the case of allyl and benzyl radicals the delocalization of the unpaired electron about the entire species. Like carbocation rearrangement radicals also undergo radical rearrangement reaction to form the more stable radical.

Answer 9

Interpretation Introduction

(b)

Interpretation:

What should student conclude regarding the alkyl rearrangement for a given reaction from a 1H NMR spectrum of the product is to be explained.

Concept introduction:

In homolysis, the radicals from a breaking of the weakest bond of the molecule give the major products. The weakest bond possesses the smallest bond dissociation energy. The stability order for radicals is methyl radical < 1oradical < 2oradical < 3oradical. Since radicals are electron-poor like carbocation the electron-donating groups increases the stability of radical. In the case of allyl and benzyl radicals the delocalization of the unpaired electron about the entire species. Like carbocation rearrangement radicals also undergo radical rearrangement reaction to form the more stable radical.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 25 - Prob. 25.1P Ch. 25 - Prob. 25.2P Ch. 25 - Prob. 25.3P Ch. 25 - Prob. 25.4P Ch. 25 - Prob. 25.5P Ch. 25 - Prob. 25.6P Ch. 25 - Prob. 25.7P Ch. 25 - Prob. 25.8P Ch. 25 - Prob. 25.9P Ch. 25 - Prob. 25.10P

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Chapter 25 Solutions