(a) Interpretation: The structures of one secondary and one tertiary alcohol that give 1-methylcyclohexene as a major acid-catalyzed dehydration product are to be drawn. The alcohol undergoing fastest reaction to give the alkene is to be stated. Concept introduction: The dehydration of an alcohol leads to the formation of alkene. This dehydration can be done by acid-catalysed mechanism. In this mechanism first step is the abstraction of proton by the hydroxide group. Second step is the removal of water to give an intermediate “carbocation”. Third step is the generation of alkene by the removal of β - hydrogen from the intermediate.

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Answer 1

Question

Chapter 10, Problem 10.8P

Interpretation Introduction

(a)

Interpretation:

The structures of one secondary and one tertiary alcohol that give 1-methylcyclohexene as a major acid-catalyzed dehydration product are to be drawn. The alcohol undergoing fastest reaction to give the alkene is to be stated.

Concept introduction:

The dehydration of an alcohol leads to the formation of alkene. This dehydration can be done by acid-catalysed mechanism. In this mechanism first step is the abstraction of proton by the hydroxide group. Second step is the removal of water to give an intermediate “carbocation”. Third step is the generation of alkene by the removal of β- hydrogen from the intermediate.

Interpretation Introduction

(b)

Interpretation:

The structures of one secondary and one tertiary alcohol that give 3-methyl-2-pentene as a major acid-catalyzed dehydration product are to be drawn. The alcohol undergoing fastest reaction to give the alkene is to be stated.

Concept introduction:

The dehydration of an alcohol leads to the formation of alkene. This dehydration can be done acid-catalysed mechanism. In this mechanism first step is the abstraction of proton by the hydroxide group. Second step is the removal of water to give an intermediate “carbocation”. Third step is the generation of alkene by the removal of β- hydrogen from the intermediate.

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Answer 2

Question

Chapter 10, Problem 10.8P

Interpretation Introduction

(a)

Interpretation:

The structures of one secondary and one tertiary alcohol that give 1-methylcyclohexene as a major acid-catalyzed dehydration product are to be drawn. The alcohol undergoing fastest reaction to give the alkene is to be stated.

Concept introduction:

The dehydration of an alcohol leads to the formation of alkene. This dehydration can be done by acid-catalysed mechanism. In this mechanism first step is the abstraction of proton by the hydroxide group. Second step is the removal of water to give an intermediate “carbocation”. Third step is the generation of alkene by the removal of β- hydrogen from the intermediate.

Interpretation Introduction

(b)

Interpretation:

The structures of one secondary and one tertiary alcohol that give 3-methyl-2-pentene as a major acid-catalyzed dehydration product are to be drawn. The alcohol undergoing fastest reaction to give the alkene is to be stated.

Concept introduction:

The dehydration of an alcohol leads to the formation of alkene. This dehydration can be done acid-catalysed mechanism. In this mechanism first step is the abstraction of proton by the hydroxide group. Second step is the removal of water to give an intermediate “carbocation”. Third step is the generation of alkene by the removal of β- hydrogen from the intermediate.

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Answer 3

Question

Chapter 10, Problem 10.8P

Interpretation Introduction

(a)

Interpretation:

The structures of one secondary and one tertiary alcohol that give 1-methylcyclohexene as a major acid-catalyzed dehydration product are to be drawn. The alcohol undergoing fastest reaction to give the alkene is to be stated.

Concept introduction:

The dehydration of an alcohol leads to the formation of alkene. This dehydration can be done by acid-catalysed mechanism. In this mechanism first step is the abstraction of proton by the hydroxide group. Second step is the removal of water to give an intermediate “carbocation”. Third step is the generation of alkene by the removal of β- hydrogen from the intermediate.

Interpretation Introduction

(b)

Interpretation:

The structures of one secondary and one tertiary alcohol that give 3-methyl-2-pentene as a major acid-catalyzed dehydration product are to be drawn. The alcohol undergoing fastest reaction to give the alkene is to be stated.

Concept introduction:

The dehydration of an alcohol leads to the formation of alkene. This dehydration can be done acid-catalysed mechanism. In this mechanism first step is the abstraction of proton by the hydroxide group. Second step is the removal of water to give an intermediate “carbocation”. Third step is the generation of alkene by the removal of β- hydrogen from the intermediate.

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Answer 4

Question

Chapter 10, Problem 10.8P

Interpretation Introduction

(a)

Interpretation:

The structures of one secondary and one tertiary alcohol that give 1-methylcyclohexene as a major acid-catalyzed dehydration product are to be drawn. The alcohol undergoing fastest reaction to give the alkene is to be stated.

Concept introduction:

The dehydration of an alcohol leads to the formation of alkene. This dehydration can be done by acid-catalysed mechanism. In this mechanism first step is the abstraction of proton by the hydroxide group. Second step is the removal of water to give an intermediate “carbocation”. Third step is the generation of alkene by the removal of β- hydrogen from the intermediate.

Interpretation Introduction

(b)

Interpretation:

The structures of one secondary and one tertiary alcohol that give 3-methyl-2-pentene as a major acid-catalyzed dehydration product are to be drawn. The alcohol undergoing fastest reaction to give the alkene is to be stated.

Concept introduction:

The dehydration of an alcohol leads to the formation of alkene. This dehydration can be done acid-catalysed mechanism. In this mechanism first step is the abstraction of proton by the hydroxide group. Second step is the removal of water to give an intermediate “carbocation”. Third step is the generation of alkene by the removal of β- hydrogen from the intermediate.

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Answer 5

Chapter 10, Problem 10.8P

Interpretation Introduction

(a)

Interpretation:

The structures of one secondary and one tertiary alcohol that give 1-methylcyclohexene as a major acid-catalyzed dehydration product are to be drawn. The alcohol undergoing fastest reaction to give the alkene is to be stated.

Concept introduction:

The dehydration of an alcohol leads to the formation of alkene. This dehydration can be done by acid-catalysed mechanism. In this mechanism first step is the abstraction of proton by the hydroxide group. Second step is the removal of water to give an intermediate “carbocation”. Third step is the generation of alkene by the removal of β- hydrogen from the intermediate.

Interpretation Introduction

(b)

Interpretation:

The structures of one secondary and one tertiary alcohol that give 3-methyl-2-pentene as a major acid-catalyzed dehydration product are to be drawn. The alcohol undergoing fastest reaction to give the alkene is to be stated.

Concept introduction:

The dehydration of an alcohol leads to the formation of alkene. This dehydration can be done acid-catalysed mechanism. In this mechanism first step is the abstraction of proton by the hydroxide group. Second step is the removal of water to give an intermediate “carbocation”. Third step is the generation of alkene by the removal of β- hydrogen from the intermediate.

Answer 6

Chapter 10, Problem 10.8P

Interpretation Introduction

(a)

Interpretation:

The structures of one secondary and one tertiary alcohol that give 1-methylcyclohexene as a major acid-catalyzed dehydration product are to be drawn. The alcohol undergoing fastest reaction to give the alkene is to be stated.

Concept introduction:

The dehydration of an alcohol leads to the formation of alkene. This dehydration can be done by acid-catalysed mechanism. In this mechanism first step is the abstraction of proton by the hydroxide group. Second step is the removal of water to give an intermediate “carbocation”. Third step is the generation of alkene by the removal of β- hydrogen from the intermediate.

Answer 7

Chapter 10, Problem 10.8P

Interpretation Introduction

(a)

Interpretation:

The structures of one secondary and one tertiary alcohol that give 1-methylcyclohexene as a major acid-catalyzed dehydration product are to be drawn. The alcohol undergoing fastest reaction to give the alkene is to be stated.

Concept introduction:

The dehydration of an alcohol leads to the formation of alkene. This dehydration can be done by acid-catalysed mechanism. In this mechanism first step is the abstraction of proton by the hydroxide group. Second step is the removal of water to give an intermediate “carbocation”. Third step is the generation of alkene by the removal of β- hydrogen from the intermediate.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The structures of one secondary and one tertiary alcohol that give 3-methyl-2-pentene as a major acid-catalyzed dehydration product are to be drawn. The alcohol undergoing fastest reaction to give the alkene is to be stated.

Concept introduction:

The dehydration of an alcohol leads to the formation of alkene. This dehydration can be done acid-catalysed mechanism. In this mechanism first step is the abstraction of proton by the hydroxide group. Second step is the removal of water to give an intermediate “carbocation”. Third step is the generation of alkene by the removal of β- hydrogen from the intermediate.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The structures of one secondary and one tertiary alcohol that give 3-methyl-2-pentene as a major acid-catalyzed dehydration product are to be drawn. The alcohol undergoing fastest reaction to give the alkene is to be stated.

Concept introduction:

The dehydration of an alcohol leads to the formation of alkene. This dehydration can be done acid-catalysed mechanism. In this mechanism first step is the abstraction of proton by the hydroxide group. Second step is the removal of water to give an intermediate “carbocation”. Third step is the generation of alkene by the removal of β- hydrogen from the intermediate.

Answer 10

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Answer 11

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Answer 13

Ch. 10 - Prob. 10.1P Ch. 10 - Prob. 10.2P Ch. 10 - Prob. 10.3P Ch. 10 - Prob. 10.4P Ch. 10 - Prob. 10.5P Ch. 10 - Prob. 10.6P Ch. 10 - Prob. 10.7P Ch. 10 - Prob. 10.8P Ch. 10 - Prob. 10.9P Ch. 10 - Prob. 10.10P

Solution Summary: The author explains how the acid-catalyzed dehydration of an alcohol leads to the formation of alkene.

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