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Solved: 2-Acetoxycyclohexyl tosylate reacts with acetate
Chapter 23, Problem 42P(choose chapter or problem)
\(2\)-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.
Equation Transcription:
Text Transcription:
2
1,2
Questions & Answers
QUESTION:
\(2\)-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.
Equation Transcription:
Text Transcription:
2
1,2
ANSWER:So