The rate constant for first order solvolysis reaction of [ (1-Bromo-1-methyl)ethyl ] benzene should be calculated. Concept introduction: Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products. Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

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Answer 1

Question

Chapter 7, Problem 55P

(a)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene should be calculated.

Concept introduction:Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

(b)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene in presence of 0.1 M LiCl should be calculated and the reason behind increased rate should be suggested.

Concept introduction: Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

(c)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene in presence of 0.1 M LiBr should be calculated and the reason behind decreased rate should be suggested.

Concept introduction: Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

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For the reaction shown, the rate of reaction when X=Cl is about the same as that when X=Br. Based on this information, which statement represents a valid deduction concerning the mechanism of this reaction? OCH2CH3 O2N NO2 NO2 (A) This is a one-step displacement reaction (B) The reaction proceeds via a benzyne intermediate (C) The C-X bond is broken in the rate-determining step (D) The C-X bond is NOT broken in the rate-determining step O2N OCH,CH3 NO2 NO2

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Answer 2

Question

Chapter 7, Problem 55P

(a)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene should be calculated.

Concept introduction:Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

(b)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene in presence of 0.1 M LiCl should be calculated and the reason behind increased rate should be suggested.

Concept introduction: Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

(c)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene in presence of 0.1 M LiBr should be calculated and the reason behind decreased rate should be suggested.

Concept introduction: Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

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Answer 3

Question

Chapter 7, Problem 55P

(a)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene should be calculated.

Concept introduction:Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

(b)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene in presence of 0.1 M LiCl should be calculated and the reason behind increased rate should be suggested.

Concept introduction: Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

(c)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene in presence of 0.1 M LiBr should be calculated and the reason behind decreased rate should be suggested.

Concept introduction: Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

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Answer 4

Question

Chapter 7, Problem 55P

(a)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene should be calculated.

Concept introduction:Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

(b)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene in presence of 0.1 M LiCl should be calculated and the reason behind increased rate should be suggested.

Concept introduction: Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

(c)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene in presence of 0.1 M LiBr should be calculated and the reason behind decreased rate should be suggested.

Concept introduction: Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

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Answer 5

Chapter 7, Problem 55P

(a)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene should be calculated.

Concept introduction:Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

(b)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene in presence of 0.1 M LiCl should be calculated and the reason behind increased rate should be suggested.

Concept introduction: Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

(c)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene in presence of 0.1 M LiBr should be calculated and the reason behind decreased rate should be suggested.

Concept introduction: Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

Answer 6

Chapter 7, Problem 55P

(a)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene should be calculated.

Concept introduction:Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

Answer 7

Chapter 7, Problem 55P

(a)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene should be calculated.

Concept introduction:Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

Answer 8

(b)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene in presence of 0.1 M LiCl should be calculated and the reason behind increased rate should be suggested.

Concept introduction: Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

Answer 9

(b)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene in presence of 0.1 M LiCl should be calculated and the reason behind increased rate should be suggested.

Concept introduction: Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

Answer 10

(c)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene in presence of 0.1 M LiBr should be calculated and the reason behind decreased rate should be suggested.

Concept introduction: Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

Answer 11

(c)

Interpretation Introduction

Interpretation: The rate constant for first order solvolysis reaction of [(1-Bromo-1-methyl)ethyl]benzene in presence of 0.1 M LiBr should be calculated and the reason behind decreased rate should be suggested.

Concept introduction: Haloalkane solvolysis with ethanol, methanol or water is a typical example for unimolecuar substitution. It proceeds via two-step mechanism. The first slow step that determines rate is the removal of leaving group from the substrate haloalkane and generates a carbocation. Since the rate is only governed by substrate alone and no other nucleophile or solvent it is termed as unimolecuar substitution. The final step is attack of nucleophile on carbocation generated and formation of racemic products.

Tertiary or secondary halides undergo fastest unimolecuar substitution as they can readily form the tertiary carbocation followed by secondary and least reactive are primary.

Answer 12

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Ch. 7.1 - Prob. 7.1E Ch. 7.2 - Prob. 7.2E Ch. 7.3 - Prob. 7.3E Ch. 7.3 - Prob. 7.5TIY Ch. 7.4 - Prob. 7.7TIY Ch. 7.5 - Prob. 7.9TIY Ch. 7.6 - Prob. 7.10E Ch. 7.7 - Prob. 7.11E Ch. 7.7 - Prob. 7.12E Ch. 7.7 - Prob. 7.13E

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