Nitrile Hydrolysis

What was the nitrile undergoing hydrolysis in this experiment?

benzonitrile

What does hydrolysis of nitriles result in?

carboxylic acids

Describe the general speed of nitrile hydrolysis reactions and why they occur at that rate.

Reaction tends to be sluggish because of the formation of a dianion intermediate

What types of solution does nitrile hydrolysis occur in? What solution was used in this particular experiment

acidic or basic aqueous solutions; basic

What occurs in a nitrile hydrolysis reaction regardless of the solution /catalyst used?

Formation of an amide intermediate

What occurs during base catalyzed hydrolysis?

The hydroxide anion adds directly to the carbon nitrogen tripple bond

What is the nucleophile in this reaction?

hydroxide

Describe the mechanism of the experiment

1. The mechanism begins with nucleophilic addition of hydroxide.

2. Next is Protonation by water to form an imidic acid and hydroxide.

3. The imidic acid will then be tautomerized to form an amide.

4. Further hydrolysis of the amide forms a carboxylic acid

What is the structure of a nitrile?

R-C≡N:

What is the structure of a hydroxide?

OH^-

What is a byproduct of nitrile hydrolysis?

Ammonium (NH₄⁺)

What is the structure of a carboxylic acid?

R−COOH

What type of reaction is nitrile hydrolysis?

addition-elimination

What is the base in the reaction?

10% sodium hydroxide

What is the product formed from the experiment?

benzoic acid

What is the byproduct of the experiment?

Ammonia NH₃(g)

What is a cyano group?

C≡N:

What is the driving force of this reaction?

Loss of ammonia gas