The mechanism for the given reaction is to be proposed. Concept introduction: In the nucleophilic addition reaction of nitriles, lone pair on the cyanide group acts as a nucleophile and abstracts the proton from ammonia under weak acidic condition. Next step is nucleophilic addition of ammonia group on the electrophilic carbon atom. Under the acidic condition, the electrohile becomes stronger. The protonated group acquires the partial positive charge on its electrophilic carbon atom. After all cyano groups get protonated, the cyclic intramolecular interaction between lone pair of NH 2 and the electrophilic carbons takes place and forms a cyclic imidine as a product.

Question

Want to see the full answer?

Answer 1

Question

Chapter 18, Problem 18.54P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be proposed.

Concept introduction:

In the nucleophilic addition reaction of nitriles, lone pair on the cyanide group acts as a nucleophile and abstracts the proton from ammonia under weak acidic condition. Next step is nucleophilic addition of ammonia group on the electrophilic carbon atom. Under the acidic condition, the electrohile becomes stronger. The protonated group acquires the partial positive charge on its electrophilic carbon atom. After all cyano groups get protonated, the cyclic intramolecular interaction between lone pair of NH2 and the electrophilic carbons takes place and forms a cyclic imidine as a product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Provide the synthesis for the following product starting with the provide starting material. More than one step is required. Show the mechanism for each reaction. Please give details.

Propose a mechanism for the following reaction and develop it.

Predict the product of the following reaction and propose a reaction mechanism

Answer 2

Question

Chapter 18, Problem 18.54P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be proposed.

Concept introduction:

In the nucleophilic addition reaction of nitriles, lone pair on the cyanide group acts as a nucleophile and abstracts the proton from ammonia under weak acidic condition. Next step is nucleophilic addition of ammonia group on the electrophilic carbon atom. Under the acidic condition, the electrohile becomes stronger. The protonated group acquires the partial positive charge on its electrophilic carbon atom. After all cyano groups get protonated, the cyclic intramolecular interaction between lone pair of NH2 and the electrophilic carbons takes place and forms a cyclic imidine as a product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 18, Problem 18.54P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be proposed.

Concept introduction:

In the nucleophilic addition reaction of nitriles, lone pair on the cyanide group acts as a nucleophile and abstracts the proton from ammonia under weak acidic condition. Next step is nucleophilic addition of ammonia group on the electrophilic carbon atom. Under the acidic condition, the electrohile becomes stronger. The protonated group acquires the partial positive charge on its electrophilic carbon atom. After all cyano groups get protonated, the cyclic intramolecular interaction between lone pair of NH2 and the electrophilic carbons takes place and forms a cyclic imidine as a product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 18, Problem 18.54P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be proposed.

Concept introduction:

In the nucleophilic addition reaction of nitriles, lone pair on the cyanide group acts as a nucleophile and abstracts the proton from ammonia under weak acidic condition. Next step is nucleophilic addition of ammonia group on the electrophilic carbon atom. Under the acidic condition, the electrohile becomes stronger. The protonated group acquires the partial positive charge on its electrophilic carbon atom. After all cyano groups get protonated, the cyclic intramolecular interaction between lone pair of NH2 and the electrophilic carbons takes place and forms a cyclic imidine as a product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 18, Problem 18.54P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be proposed.

Concept introduction:

In the nucleophilic addition reaction of nitriles, lone pair on the cyanide group acts as a nucleophile and abstracts the proton from ammonia under weak acidic condition. Next step is nucleophilic addition of ammonia group on the electrophilic carbon atom. Under the acidic condition, the electrohile becomes stronger. The protonated group acquires the partial positive charge on its electrophilic carbon atom. After all cyano groups get protonated, the cyclic intramolecular interaction between lone pair of NH2 and the electrophilic carbons takes place and forms a cyclic imidine as a product.

Answer 6

Chapter 18, Problem 18.54P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be proposed.

Concept introduction:

In the nucleophilic addition reaction of nitriles, lone pair on the cyanide group acts as a nucleophile and abstracts the proton from ammonia under weak acidic condition. Next step is nucleophilic addition of ammonia group on the electrophilic carbon atom. Under the acidic condition, the electrohile becomes stronger. The protonated group acquires the partial positive charge on its electrophilic carbon atom. After all cyano groups get protonated, the cyclic intramolecular interaction between lone pair of NH2 and the electrophilic carbons takes place and forms a cyclic imidine as a product.

Answer 7

Chapter 18, Problem 18.54P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be proposed.

Concept introduction:

In the nucleophilic addition reaction of nitriles, lone pair on the cyanide group acts as a nucleophile and abstracts the proton from ammonia under weak acidic condition. Next step is nucleophilic addition of ammonia group on the electrophilic carbon atom. Under the acidic condition, the electrohile becomes stronger. The protonated group acquires the partial positive charge on its electrophilic carbon atom. After all cyano groups get protonated, the cyclic intramolecular interaction between lone pair of NH2 and the electrophilic carbons takes place and forms a cyclic imidine as a product.

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 explains the nucleophilic addition reaction of nitriles, where lone pair on the cyanide group abstracts the proton from ammonia under weak acidic conditions.

Want to see the full answer?

Chapter 18 Solutions