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 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.MeMe,Me,.CIMeHCIAB-Ryan'sSynthesisMe'CI+75%25%МеMeMeMe...MeBMeCHCIAPoly'sSynthesis-MeМе'CI'CI++Me...CI+a trace mixture ;of constitutionalDМеchloroalkaneisomersUsing 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.9.

The formation of a major product is based upon the stability of the reaction intermediate. In the…

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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