CH3CO OTs C=0 C=0C=0 ČH3 2-acetoxycyclohexyl tosylate ČH3 ČH3 1,2-cyclohexanediol diacetate

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 6.47P: Describe the stereochemistry of the bromohydrin formed in each reaction (each reaction is...
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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.

CH3CO
OTs
C=0
C=0C=0
ČH3
2-acetoxycyclohexyl tosylate
ČH3 ČH3
1,2-cyclohexanediol diacetate
Transcribed Image Text:CH3CO OTs C=0 C=0C=0 ČH3 2-acetoxycyclohexyl tosylate ČH3 ČH3 1,2-cyclohexanediol diacetate
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