Chapter 28 - Organic Synthesis - Nitriles

Question 1

What is the nitrile functional group?

Answer 1

C =(triple bond) N

Question 2

Two different methods for production of nitriles

Answer 2

1. Reaction of haloalkanes and sodium/potassium cyanide, in ethanol
2. Reaction between aldehydes and ketones with hydrogen cyanide

Question 3

Uses of nitriles

Answer 3

• Useful intermediates in synthesis of other organic compounds, e.g. amines and carboxylic acids.

Question 4

What can nitriles be reduced to and how?

Answer 4

• They can be reduced to amines
• This can occur by reacting the nitrile with hydrogen in the presence of a nickel catalyst
  (Hydrogenation conditions)

Question 5

Hydrolysis of nitriles

• What do they form?
• What are the conditions used?

Answer 5

• They form carboxylic acids
• Conditions:
• dilute aqueous acid, e.h. HCl
• Heat (with acid)

Question 6

Product of alkylation of nitriles on benzene ring.

Conditions required?

Answer 6

• an (alkyl)benzene molecule, e.g. ethylbenzene
• and HCl
  Conditions:
• Halogen carrier catalyst

Question 7

Products of acylation of nitriles with benzene.

Conditions required?

Answer 7

• Benzene reacts with acyl chloride to produce a ketone-benzene molecule, e.g. phenylpropanone
• and HCl

Conditions:

• Halogen carrier catalyst
• Acyl chloride presence