The detailed mechanism for the given reaction of benzaldehyde with propenenitrile in presence of a catalytic amount of NaCN is to be drawn. Concept introduction: The aromatic aldehyde can be converted to a good nucleophile as carbanion by reacting it with catalytic cyanide ion. The carbanion undergoes nucleophilic addition reaction with polar π bond or conjugated polar π bond like conjugated nitrile. In the first step, the cyanide ion undergoes nucleophilic addition with aromatic aldehyde and forms a cyanohydrin. The cyanohydrin in presence of base like hydroxide ion forms a resonance stabilized carbanion, which further adds to conjugated nitrile and forms an intermediate by proton transfer. The intermediate formed then undergoes elimination of cyanide forming carbonyl derivative having cyanide functional group .

Question

Want to see the full answer?

Answer 1

Question

Chapter 18, Problem 18.71P

Interpretation Introduction

Interpretation:

The detailed mechanism for the given reaction of benzaldehyde with propenenitrile in presence of a catalytic amount of NaCN is to be drawn.

Concept introduction:

The aromatic aldehyde can be converted to a good nucleophile as carbanion by reacting it with catalytic cyanide ion. The carbanion undergoes nucleophilic addition reaction with polar π bond or conjugated polar π bond like conjugated nitrile. In the first step, the cyanide ion undergoes nucleophilic addition with aromatic aldehyde and forms a cyanohydrin. The cyanohydrin in presence of base like hydroxide ion forms a resonance stabilized carbanion, which further adds to conjugated nitrile and forms an intermediate by proton transfer. The intermediate formed then undergoes elimination of cyanide forming carbonyl derivative having cyanide functional group.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

True or false, chemistry

answer thse questions with mechanisms and steps. handwritten please!

C app.aktiv.com Draw the product of the following reaction sequence. Ignore any inorganic byproducts formed. H O 1. (CH3CH2)2CuLi, THF 2. CH3Br Drawing

Answer 2

Question

Chapter 18, Problem 18.71P

Interpretation Introduction

Interpretation:

The detailed mechanism for the given reaction of benzaldehyde with propenenitrile in presence of a catalytic amount of NaCN is to be drawn.

Concept introduction:

The aromatic aldehyde can be converted to a good nucleophile as carbanion by reacting it with catalytic cyanide ion. The carbanion undergoes nucleophilic addition reaction with polar π bond or conjugated polar π bond like conjugated nitrile. In the first step, the cyanide ion undergoes nucleophilic addition with aromatic aldehyde and forms a cyanohydrin. The cyanohydrin in presence of base like hydroxide ion forms a resonance stabilized carbanion, which further adds to conjugated nitrile and forms an intermediate by proton transfer. The intermediate formed then undergoes elimination of cyanide forming carbonyl derivative having cyanide functional group.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 18, Problem 18.71P

Interpretation Introduction

Interpretation:

The detailed mechanism for the given reaction of benzaldehyde with propenenitrile in presence of a catalytic amount of NaCN is to be drawn.

Concept introduction:

The aromatic aldehyde can be converted to a good nucleophile as carbanion by reacting it with catalytic cyanide ion. The carbanion undergoes nucleophilic addition reaction with polar π bond or conjugated polar π bond like conjugated nitrile. In the first step, the cyanide ion undergoes nucleophilic addition with aromatic aldehyde and forms a cyanohydrin. The cyanohydrin in presence of base like hydroxide ion forms a resonance stabilized carbanion, which further adds to conjugated nitrile and forms an intermediate by proton transfer. The intermediate formed then undergoes elimination of cyanide forming carbonyl derivative having cyanide functional group.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 18, Problem 18.71P

Interpretation Introduction

Interpretation:

The detailed mechanism for the given reaction of benzaldehyde with propenenitrile in presence of a catalytic amount of NaCN is to be drawn.

Concept introduction:

The aromatic aldehyde can be converted to a good nucleophile as carbanion by reacting it with catalytic cyanide ion. The carbanion undergoes nucleophilic addition reaction with polar π bond or conjugated polar π bond like conjugated nitrile. In the first step, the cyanide ion undergoes nucleophilic addition with aromatic aldehyde and forms a cyanohydrin. The cyanohydrin in presence of base like hydroxide ion forms a resonance stabilized carbanion, which further adds to conjugated nitrile and forms an intermediate by proton transfer. The intermediate formed then undergoes elimination of cyanide forming carbonyl derivative having cyanide functional group.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 18, Problem 18.71P

Interpretation Introduction

Interpretation:

The detailed mechanism for the given reaction of benzaldehyde with propenenitrile in presence of a catalytic amount of NaCN is to be drawn.

Concept introduction:

The aromatic aldehyde can be converted to a good nucleophile as carbanion by reacting it with catalytic cyanide ion. The carbanion undergoes nucleophilic addition reaction with polar π bond or conjugated polar π bond like conjugated nitrile. In the first step, the cyanide ion undergoes nucleophilic addition with aromatic aldehyde and forms a cyanohydrin. The cyanohydrin in presence of base like hydroxide ion forms a resonance stabilized carbanion, which further adds to conjugated nitrile and forms an intermediate by proton transfer. The intermediate formed then undergoes elimination of cyanide forming carbonyl derivative having cyanide functional group.

Answer 6

Chapter 18, Problem 18.71P

Interpretation Introduction

Interpretation:

The detailed mechanism for the given reaction of benzaldehyde with propenenitrile in presence of a catalytic amount of NaCN is to be drawn.

Concept introduction:

The aromatic aldehyde can be converted to a good nucleophile as carbanion by reacting it with catalytic cyanide ion. The carbanion undergoes nucleophilic addition reaction with polar π bond or conjugated polar π bond like conjugated nitrile. In the first step, the cyanide ion undergoes nucleophilic addition with aromatic aldehyde and forms a cyanohydrin. The cyanohydrin in presence of base like hydroxide ion forms a resonance stabilized carbanion, which further adds to conjugated nitrile and forms an intermediate by proton transfer. The intermediate formed then undergoes elimination of cyanide forming carbonyl derivative having cyanide functional group.

Answer 7

Chapter 18, Problem 18.71P

Interpretation Introduction

Interpretation:

The detailed mechanism for the given reaction of benzaldehyde with propenenitrile in presence of a catalytic amount of NaCN is to be drawn.

Concept introduction:

The aromatic aldehyde can be converted to a good nucleophile as carbanion by reacting it with catalytic cyanide ion. The carbanion undergoes nucleophilic addition reaction with polar π bond or conjugated polar π bond like conjugated nitrile. In the first step, the cyanide ion undergoes nucleophilic addition with aromatic aldehyde and forms a cyanohydrin. The cyanohydrin in presence of base like hydroxide ion forms a resonance stabilized carbanion, which further adds to conjugated nitrile and forms an intermediate by proton transfer. The intermediate formed then undergoes elimination of cyanide forming carbonyl derivative having cyanide functional group.

Answer 8

Expert Solution & Answer

Answer 9

Expert Solution & Answer

Answer 10

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 11

Ch. 18 - Prob. 18.1P Ch. 18 - Prob. 18.2P Ch. 18 - Prob. 18.3P Ch. 18 - Prob. 18.4P Ch. 18 - Prob. 18.5P Ch. 18 - Prob. 18.6P Ch. 18 - Prob. 18.7P Ch. 18 - Prob. 18.8P Ch. 18 - Prob. 18.9P Ch. 18 - Prob. 18.10P

Solution Summary: The author describes the reaction of benzaldehyde with propenenitrile in presence of catalytic amount of NaCN.

Concept explainers

Videos

Want to see the full answer?

Chapter 18 Solutions