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