Chapter 20.SE, Problem 23MP

Interpretation Introduction

a)

Interpretation:

The products of the reaction along with the mechanism of the reaction are to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Answer to Problem 23MP

The products of the reaction are ammonia and hexanoic acid.

The mechanism of the reaction is given below.

Formation of the amide:

Hydrolysis of the amide:

Where C₅H₁₁ = -CH₂CH₂CH₂CH₂CH₃

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in hexanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give hexanamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields hexanoic acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and hexanoic acid.

The mechanism of the reaction is given below.

Formation of the amide:

Hydrolysis of the amide:

Where C₅H₁₁ = -CH₂CH₂CH₂CH₂CH₃

Interpretation Introduction

b)

Interpretation:

The products of the reaction along with the mechanism of the reaction are to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Answer to Problem 23MP

The products of the reaction are ammonia and cyclobutanecarboxylate anion.

The mechanism of the reaction is given below.

Formation of the amide:

Hydrolysis of the amide:

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in 2-methylbutanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give 2-methylbutanamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields butanoic acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and cyclobutanecarboxylate anion.

The mechanism of the reaction is given below.

Formation of the amide:

Hydrolysis of the amide:

Interpretation Introduction

c)

Interpretation:

The product of the reaction is to be given along with the mechanism of the reaction.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine. iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Answer to Problem 23MP

The products of the reaction are ammonia and m-methylbenzamide.

The mechanism of the reaction is given below.

Formation of the amide:

Hydrolysis of the amide:

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in m-methylbenzonitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give 3-methylbenzamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields m-methylbenzoic acid. The deprotonation of the acid by the amide anion leads to the formation of the carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and m-methylbenzamide.

The mechanism of the reaction is given below.

Formation of the amide:

Hydrolysis of the amide:

Interpretation Introduction

d)

Interpretation:

The products of the reaction along with the mechanism of the reaction is to be given.

Concept introduction:

The base catalyzed nitrile hydrolysis into an amide which is then further hydrolyzed to a carboxylate anion and ammonia takes place through the following steps. i) Nucleophilic attack of the hydroxide ion to the cyanide triple bond to yield an imideanion. ii)Protonation of the imine anion by water to yield a hydroxylamine.iii) Tautomerization of the hydroxylimine to an amide iv) Hydrolysis of the amide to carboxylate anion and ammonia.

To give:

The products of the reaction along with the mechanism of the reaction.

Answer to Problem 23MP

The products of the reaction are ammonia and cyclobutanecarboxylate ion.

The mechanism of the reaction is given below.

Formation of the amide:

Hydrolysis of the amide:

Explanation of Solution

The nucleophilic attack of the hydroxide ion the nitrile carbon in cyclobutanenitrile yields an imine anion as the product which in the next step gets protonated to produce a hydroxylimine. The hydroxylamine then tautomerizes to give cyclobutanecarboxylamide.

The nucleophilic attack of the hydroxide ion on the carbonyl carbon of the amide and subsequent loss an amide ion yields cyclobutane carboxyl acid. The deprotonation of the acid by the amide anion leads to the formation of carboxylate anion with the liberation of ammonia.

Conclusion

The products of the reaction are ammonia and cyclobutanecarboxylate ion.

The mechanism of the reaction is given below.

Formation of the amide:

Hydrolysis of the amide: