Poly and B-Ryan are asked by their supervisor to synthesize (1R,3R)-1-chloro-1,3- dimethylcyclopentane. To accomplish their syntheses, Poly chooses to start from a trisubstituted alkene while B-Ryan chooses to start from a disubstituted alkene isomer. Poly's synthesis provides a mixture of isomers while B-Ryan's provides two stereoisomers. Both synthetic approaches are shown below. Me, Me, Me HCI Me A B-Ryan's Synthesis Me 'CI 75% 25% Me Me. Me, Ме.. HCI Me Me A Ме B Poly's Synthesis -Me CI 'CI + Me.. a trace mixture .CI of constitutional D Me + chloroalkane isomers Using your mechanistic knowledge of alkene reactions: (a) Explain the selectivity (regio and stereo) observed in B-Ryan's synthesis. (b) Propose a mechanism that accounts the formation of isomer C in Poly's synthesis. (c) Draw the major stereoisomer(s) formed in the "trace mixture of constitutional isomers" isolated in Poly's synthesis.
Poly and B-Ryan are asked by their supervisor to synthesize (1R,3R)-1-chloro-1,3- dimethylcyclopentane. To accomplish their syntheses, Poly chooses to start from a trisubstituted alkene while B-Ryan chooses to start from a disubstituted alkene isomer. Poly's synthesis provides a mixture of isomers while B-Ryan's provides two stereoisomers. Both synthetic approaches are shown below. Me, Me, Me HCI Me A B-Ryan's Synthesis Me 'CI 75% 25% Me Me. Me, Ме.. HCI Me Me A Ме B Poly's Synthesis -Me CI 'CI + Me.. a trace mixture .CI of constitutional D Me + chloroalkane isomers Using your mechanistic knowledge of alkene reactions: (a) Explain the selectivity (regio and stereo) observed in B-Ryan's synthesis. (b) Propose a mechanism that accounts the formation of isomer C in Poly's synthesis. (c) Draw the major stereoisomer(s) formed in the "trace mixture of constitutional isomers" isolated in Poly's synthesis.
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
Chapter6: Reactions Of Alkenes
Section: Chapter Questions
Problem 6.38P: Reaction of -pinene with borane followed by treatment of the resulting trialkylborane with alkaline...
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Question
![Poly and B-Ryan are asked by their supervisor to synthesize (1R,3R)-1-chloro-1,3-
dimethylcyclopentane. To accomplish their syntheses, Poly chooses to start from a trisubstituted
alkene while B-Ryan chooses to start from a disubstituted alkene isomer. Poly's synthesis
provides a mixture of isomers while B-Ryan's provides two stereoisomers. Both synthetic
approaches are shown below.
Me
Me,
Me,
.CI
Me
HCI
A
B-Ryan's
Synthesis
Me
'CI
+
75%
25%
Ме
Me
Me
Me...
Me
B
Me
C
HCI
A
Poly's
Synthesis
-Me
Ме
'CI
'CI
+
+
Me..
.CI
+
a trace mixture ;
of constitutional
D
Ме
chloroalkane
isomers
Using your mechanistic knowledge of alkene reactions:
(a) Explain the selectivity (regio and stereo) observed in B-Ryan's synthesis.
(b) Propose a mechanism that accounts the formation of isomer C in Poly's synthesis.
(c) Draw the major stereoisomer(s) formed in the "trace mixture of constitutional isomers" isolated
in Poly's synthesis.
9.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F2ad7f2f0-3e77-43c5-97fc-293caf8ecd8d%2Ff1aeaedc-707e-434f-ba81-7c38b9ea580c%2Fm18fre_processed.jpeg&w=3840&q=75)
Transcribed Image Text:Poly and B-Ryan are asked by their supervisor to synthesize (1R,3R)-1-chloro-1,3-
dimethylcyclopentane. To accomplish their syntheses, Poly chooses to start from a trisubstituted
alkene while B-Ryan chooses to start from a disubstituted alkene isomer. Poly's synthesis
provides a mixture of isomers while B-Ryan's provides two stereoisomers. Both synthetic
approaches are shown below.
Me
Me,
Me,
.CI
Me
HCI
A
B-Ryan's
Synthesis
Me
'CI
+
75%
25%
Ме
Me
Me
Me...
Me
B
Me
C
HCI
A
Poly's
Synthesis
-Me
Ме
'CI
'CI
+
+
Me..
.CI
+
a trace mixture ;
of constitutional
D
Ме
chloroalkane
isomers
Using your mechanistic knowledge of alkene reactions:
(a) Explain the selectivity (regio and stereo) observed in B-Ryan's synthesis.
(b) Propose a mechanism that accounts the formation of isomer C in Poly's synthesis.
(c) Draw the major stereoisomer(s) formed in the "trace mixture of constitutional isomers" isolated
in Poly's synthesis.
9.
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