Question

Give the products expected when the following tertiary amines are treated with a peroxyacid and heated.

1. N,N-dimethyl hexane-2-amine (b) N,N-diethyl hexane-2-amine

(c) cyclohexyl dimethyl amine (d) N-ethyl piperidine

Short answer

(a)

(b)

(c)

(d)

Step-by-step solution

N,N-dimethyl hexane-2-amine

This is a cope rearrangement. In this the more substituted alkene will be the major product. This product is called Hoffmann product. Here N,N-dimethyl hexane-2-amine reacts with hydrogen peroxide and then formed an alkene which on Hoffmann elimination gave the more substituted alkene as shown there.

(a)

: N,N-diethyl hexane-2-amine

This is a cope rearrangement. In this the more substituted alkene will be the major product. This product is called Hoffmann product. Here N,N-diethyl hexane-2-amine reacts with hydrogen peroxide and then formed an alkene which on Hoffmann elimination gave the more substituted alkene as shown there.

(b)

cyclohexyl dimethyl amine

This is a cope rearrangement. In this the more substituted alkene will be the major product. This product is called Hoffmann product. Here cyclohexyl dimethyl amine reacts with hydrogen peroxide and then formed an alkene which on Hoffmann elimination gave the more substituted alkene as shown there.

(c)

N-ethyl piperidine

This is a cope rearrangement. In this the more substituted alkene will be the major product. This product is called Hoffmann product. Here N-ethyl piperidine reacts with hydrogen peroxide and then formed an alkene which on Hoffmann elimination gave the more substituted alkene as shown there.

(d)