Propylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glycol, another chiral molecule.
(a) Draw the enantiomers of propylene oxide.
(b) Propose a mechanism for the acid-catalyzed hydrolysis of pure (R)-propylene oxide.
(c) Propose a mechanism for the base-catalyzed hydrolysis of pure (R)-propylene oxide.
(d) Explain why the acid-catalyzed hydrolysis of optically active propylene oxide gives a product with lower enantiomeric excess and a rotation opposite that of the product of the base-catalyzed hydrolysis.