Account for the following observations with a mechanism. (1) In 80% aqueous ethanol, compound A reacts to

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Account for the following observations with a mechanism.

(1) In 80% aqueous ethanol, compound A reacts to give compound B. Notice that trans-B is the only stereoisomer of this compound that is formed.

(2) Optically active A gives completely racemic B.

(3) The reaction of A is about 105 times faster than the analogous substitution reactions of both its stereoisomer C and chlorocyclohexane.A Figure P11.73 SPh Cl B SPh -OEt C SPh Cl

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Organic Chemistry

ISBN: 9781936221349

6th Edition

Authors: Marc Loudon, Jim Parise

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