CH3ČO OTs C=0 c-oc-o C=0C=0 ČH3 2-acetoxycyclohexyl tosylate ČH; ČH3 1,2-cyclohexanediol diacetate

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter19: Carboxylic Anhydrides, Esters, And Amides
Section: Chapter Questions
Problem 19.47P
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2-Acetoxycyclohexyl tosylate reacts with acetate ion to form 1,2-cyclohexanediol diacetate. The reaction is stereospecific—that is, the stereoisomers obtained as products depend on the stereoisomer used as a reactant. Recall that because 2-acetoxycyclohexyl tosylate has two asymmetric centers, it has four stereoisomers—two are cis and two are trans. Explain the following observations: a. Both cis reactants form an optically active trans product, but each cis reactant forms a different trans product. b. Both trans reactants form the same racemic mixture. c. A trans reactant is more reactive than a cis reactant

CH3ČO
OTs
C=0
c-oc-o
C=0C=0
ČH3
2-acetoxycyclohexyl tosylate
ČH; ČH3
1,2-cyclohexanediol diacetate
Transcribed Image Text:CH3ČO OTs C=0 c-oc-o C=0C=0 ČH3 2-acetoxycyclohexyl tosylate ČH; ČH3 1,2-cyclohexanediol diacetate
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