Determine a stepwise mechanism for the following reaction that illustrates why two substitution products are formed. Explain why 1-bromohex-2-ene reacts rapidly with a weak nucleophile (CH3OH) under Syl reaction conditions, even though it is a 1° alkyl halide. 1-bromohex-2-ene Part 1: Br CH₂CH₂CH₂CH CH₂OH The first step in the reaction proceeds according to which mechanism? Part 2: =CHCH₂ + CH₂OH Br CH₂CH₂CH₂CH=CHCH₂ Br Draw the missing resonance contributor. OCH 3 CH₂CH₂CH₂CH=CHCH₂ CH₂CH₂CH₂CH=CH-CH₂ + Br Br OCH 3 HYCHICH CHO CHI view structure + HBr a x + Br
Determine a stepwise mechanism for the following reaction that illustrates why two substitution products are formed. Explain why 1-bromohex-2-ene reacts rapidly with a weak nucleophile (CH3OH) under Syl reaction conditions, even though it is a 1° alkyl halide. 1-bromohex-2-ene Part 1: Br CH₂CH₂CH₂CH CH₂OH The first step in the reaction proceeds according to which mechanism? Part 2: =CHCH₂ + CH₂OH Br CH₂CH₂CH₂CH=CHCH₂ Br Draw the missing resonance contributor. OCH 3 CH₂CH₂CH₂CH=CHCH₂ CH₂CH₂CH₂CH=CH-CH₂ + Br Br OCH 3 HYCHICH CHO CHI view structure + HBr a x + Br
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter22: Reactions Of Benzene And Its Derivatives
Section: Chapter Questions
Problem 22.23P
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Question
![Determine a stepwise mechanism for the following reaction that illustrates why two substitution
products are formed. Explain why 1-bromohex-2-ene reacts rapidly with a weak nucleophile (CH3OH)
under Syl reaction conditions, even though it is a 1° alkyl halide.
1-bromohex-2-ene
Part 1:
Br
CH₂OH
The first step in the reaction proceeds according to which mechanism?
CH₂CH₂CH₂CH=CHCH₂ + CH₂OH
CH₂CH₂CH₂CH:
Part 2:
Br
CHCH₂
Draw the missing resonance contributor.
OCH3 +
CH3CH₂CH₂CH=CHCH₂
CH3CH₂CH₂CH=CH-CH₂ + Br
Br
OCH 3
H₂CH₂CH₂CH=CH₂
view structure
+
+ Br
HBr
X](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F127f63d9-8f89-4c37-8cc0-122cae65c6f1%2Ff03de5ce-cb21-4a67-bbaf-2a4a62df3df8%2F8h9ka4_processed.jpeg&w=3840&q=75)
Transcribed Image Text:Determine a stepwise mechanism for the following reaction that illustrates why two substitution
products are formed. Explain why 1-bromohex-2-ene reacts rapidly with a weak nucleophile (CH3OH)
under Syl reaction conditions, even though it is a 1° alkyl halide.
1-bromohex-2-ene
Part 1:
Br
CH₂OH
The first step in the reaction proceeds according to which mechanism?
CH₂CH₂CH₂CH=CHCH₂ + CH₂OH
CH₂CH₂CH₂CH:
Part 2:
Br
CHCH₂
Draw the missing resonance contributor.
OCH3 +
CH3CH₂CH₂CH=CHCH₂
CH3CH₂CH₂CH=CH-CH₂ + Br
Br
OCH 3
H₂CH₂CH₂CH=CH₂
view structure
+
+ Br
HBr
X
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