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.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter13: Substitution

Section: Chapter Questions

Problem 4E

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