.. Explain why the all cis isomer of 4-t- butylcyclohexane-1,3-diol forms an acetal with acetone but none of the other isomers do.

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
Chapter10: Alcohols
Section: Chapter Questions
Problem 10.57P
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.. Explain why the all cis isomer of 4-t-
butylcyclohexane-1,3-diol forms an acetal with
acetone but none of the other isomers do.
: You are provided with two bottles labeled
"1,2-Cyclopentanediol"; one contains a
compound of m.p. 30°C and the other, a
compound of m.p. 55°C; both compounds are
optically inactive. What simple reaction can
you perform on each of them in order to decide
which bottle should be labeled "cis" or "trans".
Transcribed Image Text:.. Explain why the all cis isomer of 4-t- butylcyclohexane-1,3-diol forms an acetal with acetone but none of the other isomers do. : You are provided with two bottles labeled "1,2-Cyclopentanediol"; one contains a compound of m.p. 30°C and the other, a compound of m.p. 55°C; both compounds are optically inactive. What simple reaction can you perform on each of them in order to decide which bottle should be labeled "cis" or "trans".
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