Chapter 22, Problem 41P

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:

1. a. Both cis reactants form an optically active trans product, but each cis reactant forms a different trans product.
2. b. Both trans reactants form the same racemic mixture.
3. c. A trans reactant is more reactive than a cis reactant.