(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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Draw the major organic substitution product or products for (2R,3S)-2-bromo-3-methylpentane reacting with the given nucleophile. Clearly drawn the stereochemistry, including a wedged bond, a dashed bond and two in-plane bonds at each stereogenic center. Omit any byproducts. Bri CH3CH2O- (conc.) Draw the major organic product or products.

Tartaric acid (C4H6O6) is a diprotic weak acid. A sample of 875 mg tartaric acid are dissolved in 100 mL water and titrated with 0.994 M NaOH. How many mL of NaOH are needed to reach the first equivalence point? How many mL of NaOH are needed to reach the second equivalence point?

Answer 2

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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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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 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