a) 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.

Question

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Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 19.SE, Problem 38MP

Interpretation Introduction

a)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 4

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 5

Interpretation Introduction

b)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 9

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 10

Interpretation Introduction

c)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 14

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 15

Interpretation Introduction

d)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 20

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Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 19.SE, Problem 38MP

Interpretation Introduction

a)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 4

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 5

Interpretation Introduction

b)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 9

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 10

Interpretation Introduction

c)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 14

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 15

Interpretation Introduction

d)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 20

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 19.SE, Problem 38MP

Interpretation Introduction

a)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 4

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 5

Interpretation Introduction

b)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 9

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 10

Interpretation Introduction

c)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 14

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 15

Interpretation Introduction

d)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 20

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 19.SE, Problem 38MP

Interpretation Introduction

a)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 4

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 5

Interpretation Introduction

b)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 9

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 10

Interpretation Introduction

c)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 14

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 15

Interpretation Introduction

d)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 20

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Answer 5

Chapter 19.SE, Problem 38MP

Interpretation Introduction

a)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 4

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 5

Interpretation Introduction

b)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 9

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 10

Interpretation Introduction

c)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 14

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 15

Interpretation Introduction

d)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 20

Answer 6

Chapter 19.SE, Problem 38MP

Interpretation Introduction

a)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 4

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 5

Answer 7

Chapter 19.SE, Problem 38MP

Interpretation Introduction

a)

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.

Answer 8

Expert Solution

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 3

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

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.

Answer 13

Conclusion

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 4

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 5

Answer 14

Interpretation Introduction

b)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 9

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 10

Answer 15

Interpretation Introduction

b)

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.

Answer 16

Expert Solution

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 8

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

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.

Answer 21

Conclusion

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 9

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 10

Answer 22

Interpretation Introduction

c)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 14

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 15

Answer 23

Interpretation Introduction

c)

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.

Answer 24

Expert Solution

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 13

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

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.

Answer 29

Conclusion

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 14

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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 15

Answer 30

Interpretation Introduction

d)

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

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 20

Answer 31

Interpretation Introduction

d)

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.

Answer 32

Expert Solution

Answer to Problem 38MP

The product of the Wolff-Kishner reduction reaction shown is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, 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.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 19.SE, Problem 38MP , additional homework tip 18

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

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.