(a) Propose a mechanism for the conversion of cis-hex-3-ene to the epoxide (3,4-epoxyhexane)and the ring-opening reaction to give the glycol, hexane-3,4-diol. In your mechanism, payparticular attention to the stereochemistry of the intermediates and products.(b) Repeat part (a) for trans-hex-3-ene. Compare the products obtained from cis- andtrans-hex-3-ene. Is this reaction sequence stereospecific?

(a) Propose a mechanism for the conversion of cis-hex-3-ene to the epoxide (3,4-epoxyhexane)and the ring-opening reaction to give the glycol, hexane-3,4-diol. In your mechanism, payparticular attention to the stereochemistry of the intermediates and products.(b) Repeat part (a) for trans-hex-3-ene. Compare the products obtained from cis- andtrans-hex-3-ene. Is this reaction sequence stereospecific?

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

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.64P

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