26. Amines

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. <IMAGE>

(•) 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