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. CH,C=N in H,SO, Br NHCCH3 NH2 1-Bromoadamantane Amantadine (a) Propose a mechanism for the transformation in Step 1. (b) Describe experimental conditions to bring about Step 2.

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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.
CH,C=N
in H,SO,
Br
NHCCH3
NH2
1-Bromoadamantane
Amantadine
(a) Propose a mechanism for the transformation in Step 1.
(b) Describe experimental conditions to bring about Step 2.
Transcribed Image Text: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. CH,C=N in H,SO, Br NHCCH3 NH2 1-Bromoadamantane Amantadine (a) Propose a mechanism for the transformation in Step 1. (b) Describe experimental conditions to bring about Step 2.
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