Problem

Propylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glyc...

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

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