Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
Question
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Chapter 19.SE, Problem 38MP
Interpretation Introduction

a)

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  1

Interpretation:

The product of the Wolff-Kishner reduction reaction shown is to be given. The electron-pushing mechanism, beginning from the hydrazone intermediate is to be provided.

Concept introduction:

In Wolff-Kishner reduction aldehydes and ketones react with hydrazine in the presence of a base to yield alkanes. First a hydrazone is formed which is then converted into an alkane.

To give:

The product of the Wolff-Kishner reduction reaction shown.

To provide:

The electron-pushing mechanism, beginning from the hydrazone intermediate.

Expert Solution
Check Mark

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  2

The electron-pushing mechanism for the formation of the alkane, beginning from the hydrazone intermediate, is given below.

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  3

Explanation of Solution

The hydroxide ion from KOH abstracts a weakly acidic H from –NH2 of the hydrazone of isopropyl phenyl ketone to yield a carbanion which picks up a proton to yield a neutral intermediate. Deprotonation of the remaining hydrogen on N by the hydroxide ion occurs with the eliminartion of nitrogen to yield another carbanion which is protonated to give the alkane, ethyl benzene, as the product.

Conclusion

The product of the Wolff-Kishner reduction reaction shown is

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  4

The electron-pushing mechanism, beginning from the hydrazone intermediate is given below.

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  5

Interpretation Introduction

b)

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  6

Interpretation:

The product of the Wolff-Kishner reduction reaction shown is to be given. The electron-pushing mechanism, beginning from the hydrazone intermediate is to be provided.

Concept introduction:

In Wolff-Kishner reduction aldehydes and ketones react with hydrazine in the presence of a base to yield alkanes. First a hydrazone is formed which is then converted into an alkane.

To give:

The product of the Wolff-Kishner reduction reaction shown.

To provide:

The electron-pushing mechanism the formation of the alkane beginning from the hydrazone intermediate.

Expert Solution
Check Mark

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  7

The electron-pushing mechanism the formation of the alkane, beginning from the hydrazone intermediate, is given below.

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  8

Explanation of Solution

The hydroxide ion from KOH abstracts a weakly acidic H from –NH2 of the hydrazone of diethyl ketone to yield a carbanion which picks up a proton to yield a neutral intermediate. Deprotonation of the remaining hydrogen on N by the hydroxide ion occurs with the eliminartion of nitrogen to yield another carbanion which is protonated to give the alkane, n-pentane, as the product.

Conclusion

The product of the Wolff-Kishner reduction reaction shown is

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  9

The electron-pushing mechanism, beginning from the hydrazone intermediate is given below.

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  10

Interpretation Introduction

c)

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  11

Interpretation:

The product of the Wolff-Kishner reduction reaction shown is to be given. The electron-pushing mechanism, beginning from the hydrazone intermediate is to be provided.

Concept introduction:

In Wolff-Kishner reduction aldehydes and ketones react with hydrazine in the presence of a base to yield alkanes. First a hydrazone is formed which is then converted into an alkane.

To give:

The product of the Wolff-Kishner reduction reaction shown.

To provide:

The electron-pushing mechanism the formation of the alkane beginning from the hydrazone intermediate.

Expert Solution
Check Mark

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  12

The electron-pushing mechanism the formation of the alkane, beginning from the hydrazone intermediate, is given below.

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  13

Explanation of Solution

The hydroxide ion from KOH abstracts a weakly acidic H from –NH2 of the hydrazone of the ketone to yield a carbanion which picks up a proton to yield a neutral intermediate. Deprotonation of the remaining hydrogen on N by the hydroxide ion occurs with the eliminartion of nitrogen to yield another carbanion which is protonated to give the alkane as the product.

Conclusion

The product of the Wolff-Kishner reduction reaction shown is

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  14

The electron-pushing mechanism, beginning from the hydrazone intermediate is given below.

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  15

Interpretation Introduction

d)

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  16

Interpretation:

The product of the Wolff-Kishner reduction reaction shown is to be given. The electron-pushing mechanism, beginning from the hydrazone intermediate is to be provided.

Concept introduction:

In Wolff-Kishner reduction aldehydes and ketones react with hydrazine in the presence of a base to yield alkanes. First a hydrazone is formed which is then converted into an alkane.

To give:

The product of the Wolff-Kishner reduction reaction shown.

To provide:

The electron-pushing mechanism, beginning from the hydrazone intermediate.

Expert Solution
Check Mark

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  17

The electron-pushing mechanism for the formation of the alkane beginning from the hydrazone intermediate, is given below.

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  18

Explanation of Solution

The hydroxide ion from KOH abstracts a weakly acidic H from –NH2 of the hydrazone of ketone to yield a carbanion which picks up a proton to yield a neutral intermediate. Deprotonation of the remaining hydrogen on N by the hydroxide ion occurs with the eliminartion of nitrogen to yield another carbanion which is protonated to give the alkane as the product.

Conclusion

The product of the Wolff-Kishner reduction reaction shown is

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  19

The electron-pushing mechanism for the formation of the alkane beginning from the hydrazone intermediate, is given below.

Organic Chemistry, Chapter 19.SE, Problem 38MP , additional homework tip  20

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Chapter 19 Solutions

Organic Chemistry

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