2)dimethylcyclopentane. To accomplish their syntheses, Poly chooses to start from a trisubstitutedalkene while B-Ryan chooses to start from a disubstituted alkene isomer. Poly's synthesisprovides a mixture of isomers while B-Ryan's provides two stereoisomers. Both syntheticapproaches are shown below.Poly and B-Ryan are asked by their supervisor to synthesize (1R,3R)-1-chloro-1,3-MeМе.Me,.CIAMeHCI„MeB-Ryan'sSynthesis'CI+75%25%Me,Me.Me.,Me,.CI'MeMeHCI-MeB MePoly'sSynthesis'CI++Me.,.CIMea trace mixture :jof constitutional:chloroalkaneisomersUsing 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" isolatedin Poly's synthesis.

Answered: Image /qna-images/answer/cfdc45f3-976f-4cc2-b081-f8d1d1eef42a.jpg

2) 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. Poly and B-Ryan are asked by their supervisor to synthesize (1R,3R)-1-chloro-1,3- Me Me. Ме .CI A Me HCI „Me B-Ryan's Synthesis 'CI + 75% 25% Me, Me. Me., Me, HCI .CI Me B Me Poly's Synthesis -Me "Me 'CI + + Me., a trace mixture: jof constitutional: chloroalkane isomers .CI Me 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.

2) 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. Poly and B-Ryan are asked by their supervisor to synthesize (1R,3R)-1-chloro-1,3- Me Me. Ме .CI A Me HCI „Me B-Ryan's Synthesis 'CI + 75% 25% Me, Me. Me., Me, HCI .CI Me B Me Poly's Synthesis -Me "Me 'CI + + Me., a trace mixture: jof constitutional: chloroalkane isomers .CI Me 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.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Concept explainers

Amines

Amines are organic compounds with a nitrogen atom having a lone pair of electrons on it. They are derived from ammonia (NH3) wherein hydrogen atoms are substituted by an aryl or alkyl group.

Question

2)
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.
Poly and B-Ryan are asked by their supervisor to synthesize (1R,3R)-1-chloro-1,3-
Me
Ме.
Me,
.CI
A
Me
HCI
„Me
B-Ryan's
Synthesis
'CI
+
75%
25%
Me,
Me.
Me.,
Me,
.CI
'Me
Me
HCI
-Me
B Me
Poly's
Synthesis
'CI
+
+
Me.,
.CI
Me
a trace mixture :
jof constitutional:
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.

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