26. Amines

Using any necessary reagents, show how you would accomplish the following syntheses.

(e)

(f)

Predict the products of the following reactions:

(c)

(d)

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

d.

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

c.

A tertiary amine reacts with hydrogen peroxide to form a tertiary amine oxide.

Tertiary amine oxides undergo a reaction similar to the Hofmann elimination reaction (Section 10.10), called a Cope elimination. In this reaction, a tertiary amine oxide, rather than a quaternary ammonium ion, undergoes elimination. A strong base is not needed for a Cope elimination because the amine oxide acts as its own base.

Does the Cope elimination have an alkene-like transition state or a carbanion-like transition state?

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

(a) N,N-dimethylhexan-2-amine

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

(b) N,N-diethylhexan-2-amine

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

(c) cyclohexyldimethylamine

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

(d) N-ethylpiperidine

Predict the products of the following reactions:

(i) <IMAGE of reaction>

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

a.

b.

Predict the products from the reactions of the following amines with sodium nitrite in dilute HCl.

(b) N-ethylhexan-2-amine 

Predict the products of the following reactions:

(g)

Predict the products of the following reactions:

(i)