Nitriles and Hydroxynitriles

Question 1

What is the functional group of nitriles?

Answer 1

-C—N

Question 2

What are the functional groups in hydroxynitriles?

Answer 2

-OH and -C—N

Question 3

How do you name nitriles?

Answer 3

-anenitrile
eg, pentanenitrile

Question 4

How are nitriles synthesised?

Answer 4

By reacting haloalkanes with CN- and ethanol. The ethanol prevents H2O reacting with the haloalkane, forming an alcohol
Source can be KCN/NaCN

Question 5

What mechanism does synthesis of nitriles work by?

Answer 5

Nucleophillic substitution. Extends carbon chain

Question 6

How are hydroxynitriles synthesised?

Answer 6

Reacting carbonyl compounds like ketones and aldehydes with HCN from H2SO4/NaOH mixture

Question 7

What is the mechanism of synthesis of hydroxynitriles?

Answer 7

Nucleophilic addition

Question 8

How are nitriles used to synthesise amines?

Answer 8

Nitriles are reduced with H2/Ni
- You need 2 mols of H2 for each nitrile group to add H2 to the carbon and H2 to the nitrogen

Question 9

How are nitriles used to synthesise carboxylic acids?

Answer 9

They are hydrolysed to carboxylic acids with HOT AQUEOUS HCl (HCl and 2H2O)
—> carboxylic acid and NH4Cl