2-Acetoxycyclohexyl tosylate reacts with acetate ion to form 1,2-cyclohexanediol
Chapter 22, Problem 42(choose chapter or problem)
2-Acetoxycyclohexyl tosylate reacts with acetate ion to form 1,2-cyclohexanediol diacetate. The reaction is stereospecifi cthat 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 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. CH3CO 2-acetoxycyclohexyl tosylate O O OTs C O CH3 1,2-cyclohexanediol diacetate O O C O CH3 C O CH3
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