in a much lower ratio [Reaction 2, 55:45 ratio]. What is the major product for reaction 1? OtBu= 0 H₂C CH₂ CH₂ H₂C CHI to HỔ OtBu Ll CH₂ OIBU Product 1 + H₂C CH₂ OtBu Product 2 Reaction 1 99.1

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
Section16.SE: Something Extra
Problem 30MP: The carbocation electrophile in a Friede1-Crafts reaction can be generated by an alternate means...
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Electrophilic addition of hydroiodic acid to (3S)-3-tert-
butoxypent-1-ene gives an unequal mixture of two products
[Reaction 1, 99:1 ratio]. The same reaction carried out on
(3S)-3-methoxy-pent-1-ene also gave two stereoisomers albeit
in a much lower ratio [Reaction 2, 55:45 ratio]. What is
the major product for reaction 1?
0
HỌC LỊCH
CH₂
OtBu =
o
OCH₂=CH₂
Product 2
Product 1
H₂C
H₂C
Y CH₂
OtBu
CH₂H₂C
CH₂
OCH,
HI
ECO
Ⓒ1Bu
Product 1
H₂C
CH₁₂ H₂C
H
+
OCH₂
Product 3
CH₂
CH₂
OtBu
Product 2
H₂C T
CH₂
OCH,
Product 4
Reaction 1
99:1
Reaction 2
50:45
Transcribed Image Text:Electrophilic addition of hydroiodic acid to (3S)-3-tert- butoxypent-1-ene gives an unequal mixture of two products [Reaction 1, 99:1 ratio]. The same reaction carried out on (3S)-3-methoxy-pent-1-ene also gave two stereoisomers albeit in a much lower ratio [Reaction 2, 55:45 ratio]. What is the major product for reaction 1? 0 HỌC LỊCH CH₂ OtBu = o OCH₂=CH₂ Product 2 Product 1 H₂C H₂C Y CH₂ OtBu CH₂H₂C CH₂ OCH, HI ECO Ⓒ1Bu Product 1 H₂C CH₁₂ H₂C H + OCH₂ Product 3 CH₂ CH₂ OtBu Product 2 H₂C T CH₂ OCH, Product 4 Reaction 1 99:1 Reaction 2 50:45
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