Question

Amantadine is effective in preventing infections caused by the influenza A virus and in treating established illnesses. It is thought to block a late stage in the assembly of the virus. Amantadine is synthesized by treating 1-bromoadamantane with acetonitrile in sulfuric acid to give N-adamantylacetamide, which is then converted to amantadine.
(a) Propose a mechanism for the transformation in Step 1.
(b) Describe experimental conditions to bring about Step 2.

Answer 1

Answer:

See image attached

Explanation:

a)

The full reaction mechanism of step 1 was obtained from Bartleby and attached to this answer. The steps involved in the reaction are:

1) Loss of Br- and formation of a carbocation

2) Attack of CH3CN on the carbocation

4) Formation of a quaternary nitrogen intermediate

5) Attack of water on the quaternary nitrogen intermediate

6) Loss of the water molecule

5) Formation of the amide product

b)

i) sodium hydroxide

ii) HCl