(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

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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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3-Chloro-2-methylpropene reacts with sodium methoxide in methanol to form 3-methoxy-2-methylpropene. For each of the following changes in the reaction conditions, state whether the reaction rate would increase, decrease, or remain the same. Explain your reasoning. In some cases the identity of the major organic product would be expected to change; in such cases, give the expected major product. (a) dimethyl sulfoxide (DMSO) is used in place of methanol (b) methanol is used by itself without sodium methoxide (c) 1-chloro-2,2,-dimethylpropane is used in place of 3-chloro-2-methylpropene

2. There are two isomeric alkenes that can produce the first alcohol shown below as the major product with one set of reagents, but with other reagents, the same two alkenes will produce the second alcohol as the major product. H3C OH H3C, ОН H3C. CH3 (a) Draw the structure of the two alkenes described above. (b) Provide the reagents required to obtain each of the two alcohols. (c) Write out the arrow-pushing mechanism that produces the second alcohol.

For each pair of compounds, predict which compound has a higher boiling point. then explain why that compound has a higher boiling point. (a) isopropyl bromide and n-butyl bromide (b) isopropyl chloride and tert-butyl bromide (c) 1-bromobutane and 1-chlorobutane

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 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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