(a) (c) (d) CH3 CH2 Br CI H CH3 + CH₂ CH₂. CH3 DBN "bulky base" Br CH CH3 CH₂CH3 CH3 + CH3OH O + NaSH + Na OCH3 25°C SN1 El SN2 E2 SN1 SN2 El E2 SN1 SN2 E1 SN1 E1 E2 SN2 E2

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter16: Synthesis Workshop 1
Section: Chapter Questions
Problem 46CTQ
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For each of the following reactions, circle the mechanism(s) you would expect to see and provide the major product(s). Write NR for no reaction, if you don’t expect any reaction.

3
(b)
(c)
(d)
CH3-
CI
CH₂ CH₂
Br
CH3
DBN
"bulky base"
CH₂
MICH3
Br
CH
CH3
"CH₂CH3
CH3
+ CH3OH
+ NaSH
+ Na OCH3
25°C
SN1
E1
SN1
El
SN1
E1
SN2
E2
SN2
E2
SN2
E2
SN1 SN2
E1
E2
Transcribed Image Text:3 (b) (c) (d) CH3- CI CH₂ CH₂ Br CH3 DBN "bulky base" CH₂ MICH3 Br CH CH3 "CH₂CH3 CH3 + CH3OH + NaSH + Na OCH3 25°C SN1 E1 SN1 El SN1 E1 SN2 E2 SN2 E2 SN2 E2 SN1 SN2 E1 E2
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