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 issynthesized from adamantane by the following sequence:CH₂=CHBrAlBr3(2)Adamantane=D₂.-6.(3)-BrBr(4)ØBr₂(1)a Step 2 proceeds via the following mechanism:1-bromoadamantane(5)BrSnFChemDoodleRimantadine1. 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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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:

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:

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Section21.SE: Something Extra

Problem 60AP

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Question

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 == ✔

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