Question

What products are obtained when the following tertiary amines react with hydrogen peroxide followed by heat?

a.

b.

c.

d.

Short answer

a.

b.

c.

d.

Step-by-step solution

Cope elimination

Cope elimination is an elimination reaction of N-oxide to form alkene and hydroxylamine. In this reaction hydrogen peroxide is used for oxidation of tertiary amine followed by heat for products.

Mechanism of cope elimination

Oxidation of tertiary amine by hydrogen peroxide.

Oxidation of tertiary amine

Step two: Tertiary amine oxide on heating form alkene and hydroxylamine.

Part ‘a’

The two products formed are alkene and hydroxylamine after oxidation with peroxide and heating. Products are given below:

Products

Part ‘b’

The two products formed are given below:

The following products are formed as hydrogen peroxide on reaction with tertiary amine forms tertiary amine oxide which on heating will give an alkene and hydroxylamine.

Part ‘c’

This reaction will form two products which are given below:

Part ‘d’

This reaction gives two products namely an alkene and hydroxylamine but here the tertiary amine is part of cyclic ring so hydroxyl group is added to amine nitrogen as in any other case and alkene is formed at adjacent carbon to nitrogen as in other cases.

The product is given below: