A graduate student was studying enzymatic reductions of cyclohexanones 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 repurified 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 stereocenters?
(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.
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