A graduate student was studying enzymatic reductions of cyclohexan ones when she encountered some interesting chemistry. When she used an enzyme and NADPH to reduce the following ketone, she was surprised to find that the product was optically active. She carefully re-purified the product so that no enzyme, NADPH, or other contaminants were present. Still, the product was optically active.

(a) Does the product have any asymmetric carbon atoms or other stereo-centers?
(b) Is the product capable of showing optical activity? If it is, explain how.
(c) If this reaction could be accomplished using H2 and a nickel catalyst, would the product be optically active? Explain.

Transcribed Image Text:

COOH но COOH NADPH enzyme optically active