Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane by the following sequence:

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What is the structure of nucleophile 3? Thank you.

Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is
synthesized from adamantane by the following sequence:
CH₂=CHBr
AlBr3
(2)
Adamantane
=D₂.-6.
(3)
-Br
Br
(4)
Ø
Br₂
(1)
a Step 2 proceeds via the following mechanism:
1-bromoadamantane
(5)
Br
SnF
ChemDoodle
Rimantadine
1. AlBr, acts as a Lewis acid to yield carbocation 1;
2. Bromoethene acts as a nucleophile to give carbocation 2;
3. Carbocation 2 reacts with nucleophile 3 to give the product of reaction 2.
Work out this mechanism on a separate sheet of paper and then draw the structure of nucleophile 3.
NH₂
==starting points == ✔
Transcribed Image Text:Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane by the following sequence: CH₂=CHBr AlBr3 (2) Adamantane =D₂.-6. (3) -Br Br (4) Ø Br₂ (1) a Step 2 proceeds via the following mechanism: 1-bromoadamantane (5) Br SnF ChemDoodle Rimantadine 1. AlBr, acts as a Lewis acid to yield carbocation 1; 2. Bromoethene acts as a nucleophile to give carbocation 2; 3. Carbocation 2 reacts with nucleophile 3 to give the product of reaction 2. Work out this mechanism on a separate sheet of paper and then draw the structure of nucleophile 3. NH₂ ==starting points == ✔
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