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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.

1 Answer

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Answer:

See image attached

Step-by-step 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

Amantadine is effective in preventing infections caused by the influenza A virus and-example-1
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