Solved: 2-Acetoxycyclohexyl tosylate reacts with acetate ion to form 1,2-cyclohexanediol
Chapter 22, Problem 41(choose chapter or problem)
2-Acetoxycyclohexyl tosylate reacts with acetate ion to form 1,2-cyclohexanediol diacetate. The reaction is stereospecificthat is, the stereoisomersobtained as products depend on the stereoisomer used as a reactant. Recall that because 2-acetoxycyclohexyl tosylate has two asymmetric centers, it hasfour stereoisomerstwo 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.
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