a) Interpretation: The product of the reaction shown is to be given. Concept introduction: Ethers are cleaved by strong acids. The cleavage takes place either by S N 1 or S N 2 mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S N 2 mechanism. The Br - or I - attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide . Ethers with a tertiary, benzylic or an allylic group cleave either by S N 1 or E 1 mechanism as these can produce stable carbocations yielding alkenes and alcohols. To give: The product of the reaction shown.

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Answer 1

Question

Chapter 18.3, Problem 7P

Interpretation Introduction

a)

Interpretation:

The product of the reaction shown is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br^- or I^- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E¹ mechanism as these can produce stable carbocations yielding alkenes and alcohols.

To give:

The product of the reaction shown.

Interpretation Introduction

b)

Interpretation:

The product of the reaction shown is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br^- or I^- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or a allylic group cleave either by S_N¹ or E¹ mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The product of the reaction shown.

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Answer 2

Question

Chapter 18.3, Problem 7P

Interpretation Introduction

a)

Interpretation:

The product of the reaction shown is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br^- or I^- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E¹ mechanism as these can produce stable carbocations yielding alkenes and alcohols.

To give:

The product of the reaction shown.

Interpretation Introduction

b)

Interpretation:

The product of the reaction shown is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br^- or I^- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or a allylic group cleave either by S_N¹ or E¹ mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The product of the reaction shown.

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See solution

Answer 3

Question

Chapter 18.3, Problem 7P

Interpretation Introduction

a)

Interpretation:

The product of the reaction shown is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br^- or I^- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E¹ mechanism as these can produce stable carbocations yielding alkenes and alcohols.

To give:

The product of the reaction shown.

Interpretation Introduction

b)

Interpretation:

The product of the reaction shown is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br^- or I^- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or a allylic group cleave either by S_N¹ or E¹ mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The product of the reaction shown.

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See solution

Answer 4

Question

Chapter 18.3, Problem 7P

Interpretation Introduction

a)

Interpretation:

The product of the reaction shown is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br^- or I^- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E¹ mechanism as these can produce stable carbocations yielding alkenes and alcohols.

To give:

The product of the reaction shown.

Interpretation Introduction

b)

Interpretation:

The product of the reaction shown is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br^- or I^- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or a allylic group cleave either by S_N¹ or E¹ mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The product of the reaction shown.

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Answer 5

Chapter 18.3, Problem 7P

Interpretation Introduction

a)

Interpretation:

The product of the reaction shown is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br^- or I^- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E¹ mechanism as these can produce stable carbocations yielding alkenes and alcohols.

To give:

The product of the reaction shown.

Interpretation Introduction

b)

Interpretation:

The product of the reaction shown is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br^- or I^- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or a allylic group cleave either by S_N¹ or E¹ mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The product of the reaction shown.

Answer 6

Chapter 18.3, Problem 7P

Interpretation Introduction

a)

Interpretation:

The product of the reaction shown is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br^- or I^- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E¹ mechanism as these can produce stable carbocations yielding alkenes and alcohols.

To give:

The product of the reaction shown.

Answer 7

Chapter 18.3, Problem 7P

Interpretation Introduction

a)

Interpretation:

The product of the reaction shown is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br^- or I^- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E¹ mechanism as these can produce stable carbocations yielding alkenes and alcohols.

To give:

The product of the reaction shown.

Answer 8

Interpretation Introduction

b)

Interpretation:

The product of the reaction shown is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br^- or I^- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or a allylic group cleave either by S_N¹ or E¹ mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The product of the reaction shown.

Answer 9

Interpretation Introduction

b)

Interpretation:

The product of the reaction shown is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br^- or I^- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or a allylic group cleave either by S_N¹ or E¹ mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The product of the reaction shown.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 18.1 - Name the following ethers:Ch. 18.2 - Why do you suppose only symmetrical ethers are...Ch. 18.2 - How would you prepare the following ethers using a...Ch. 18.2 - Review the mechanism of oxymercuration shown in...Ch. 18.2 - How would you prepare the following ethers? Use...Ch. 18.2 - Prob. 6P Ch. 18.3 - Prob. 7P Ch. 18.3 - Write the mechanism of the acid-induced cleavage...Ch. 18.3 - Why are HI and HBr more effective than HCl in...Ch. 18.4 - What product would you expect from Claisen...

Solution Summary: The author explains the products of the reaction shown. Ethers are cleaved by strong acids.

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Chapter 18 Solutions