What type of reaction is occuring in step 3? (halogenation, hydrohalogenation, reduction, keto–enol tautomerism, dehydrohalogenation, acid-catalyzed hydration, base-catalyzed hydration) 2. Which reagent is necessary for step 3? (Br2, HBr, H2/Pt, NaNH2, H20/H2SO4/HgSO4)

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter24: Amines And Heterocycles
Section24.SE: Something Extra
Problem 40MP
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1. What type of reaction is occuring in step 3? (halogenation, hydrohalogenation, reduction, keto–enol tautomerism, dehydrohalogenation, acid-catalyzed hydration, base-catalyzed hydration)

2. Which reagent is necessary for step 3? (Br2, HBr, H2/Pt, NaNH2, H20/H2SO4/HgSO4)

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
ID
(2)
AlBr3
0
Adamantane
(4)
Br
Br₂
(1)
-Br
1-bromoadamantane
(5)
Br
(3)
Ø
Rimantadine
NH₂
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 ID (2) AlBr3 0 Adamantane (4) Br Br₂ (1) -Br 1-bromoadamantane (5) Br (3) Ø Rimantadine NH₂
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