26. Amines

What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?

a. pentylamine

What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?

b. isohexylamine

Show how Gabriel syntheses are used to prepare the following amines.

(a) benzylamine

(b) hexan-1-amine

(c) γ-aminobutyric acid

What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?

c. benzylamine

What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?

d. cyclohexylamine

Predict the product(s) of the reactions shown.

(i)

The Gabriel synthesis is most frequently done with 1° alkyl halides. Why is it less successful with more substituted halides?

Several additional amine syntheses are effectively limited to making primary amines. The reduction of azides and nitro compounds and the Gabriel synthesis leave the carbon chain unchanged. Formation and reduction of a nitrile adds one carbon atom. Show how these amine syntheses can be used for the following conversions.

(a) allyl bromide → allylamine