a) Interpretation: The structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocation is to be proposed. Concept introduction: The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon. To propose: The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Question

piperidine undergoes the series of reactions shown here, 1,4-pentadiene is obtained as the product. When the four different methyl-substitutedpiperidines undergo the same series of reactions, each forms a different diene: 1,5-hexadiene; 1,4-pentadiene; 2-methyl-1,4-pentadiene; and3-methyl-1,4-pentadiene. Which methyl-substituted piperidine forms which diene?

Answer 1

Question

Chapter 7.SE, Problem 60AP

Interpretation Introduction

a)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocation is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

b)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation can rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

c)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

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piperidine undergoes the series of reactions shown here, 1,4-pentadiene is obtained as the product. When the four different methyl-substitutedpiperidines undergo the same series of reactions, each forms a different diene: 1,5-hexadiene; 1,4-pentadiene; 2-methyl-1,4-pentadiene; and3-methyl-1,4-pentadiene. Which methyl-substituted piperidine forms which diene?

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The scheme below shows two reactions starting from compound Z. Heating Z results in a loss of CO, to give the product shown on the left. Treating compound Z with strong acid results in an intramolecular reaction that leads to product B. Determine and draw the structure of compound B gnly. heat H* В + H,0 HO C9H1404 C9H1203 C3H402

Answer 2

Question

Chapter 7.SE, Problem 60AP

Interpretation Introduction

a)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocation is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

b)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation can rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

c)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

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Answer 3

Question

Chapter 7.SE, Problem 60AP

Interpretation Introduction

a)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocation is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

b)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation can rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

c)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

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Answer 4

Question

Chapter 7.SE, Problem 60AP

Interpretation Introduction

a)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocation is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

b)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation can rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

c)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

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Answer 5

Chapter 7.SE, Problem 60AP

Interpretation Introduction

a)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocation is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

b)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation can rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

c)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Answer 6

Chapter 7.SE, Problem 60AP

Interpretation Introduction

a)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocation is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Answer 7

Chapter 7.SE, Problem 60AP

Interpretation Introduction

a)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocation is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Answer 8

Interpretation Introduction

b)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation can rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Answer 9

Interpretation Introduction

b)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation can rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Answer 10

Interpretation Introduction

c)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Answer 11

Interpretation Introduction

c)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Answer 12

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Answer 23

Ch. 7.2 - Calculate the degree of unsaturation in each of...Ch. 7.2 - Prob. 2P Ch. 7.2 - Diazepam, marketed as an antianxiety medication...Ch. 7.3 - Give IUPAC names for the following compounds:Ch. 7.3 - Prob. 5P Ch. 7.3 - Prob. 6P Ch. 7.3 - Prob. 7P Ch. 7.4 - Prob. 8P Ch. 7.4 - Prob. 9P Ch. 7.4 - Prob. 10P

Solution Summary: The author proposes the structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocated.

Chapter 7 Solutions