Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
9th Edition
ISBN: 9781292151229
Author: Wade, LeRoy G.
Publisher: PEARSON
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Chapter 5, Problem 5.39SP

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.

Chapter 5, Problem 5.39SP, A graduate student was studying enzymatic reductions of cyclohexanones when she encountered some

  1. a. (a) Does the product have any asymmetric carbon atoms or other stereocenters?
  2. b. (b) Is the product capable of showing optical activity? If it is, explain how.
  3. c. (c) If this reaction could be accomplished using H2 and a nickel catalyst, would the product be optically active? Explain.
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A compound A, C7H12, was found to be optically active. On catalytic reduction over platinum catalyst, 2 equivalents of hydrogen were absorbed, yielding compound B, C7H16. On ozonolysis of A, two fragments were obtained. One fragment was identified as acetic acid. The other fragment, compound C, was an optically active carboxylic acid, C5H10O2. Write the reactions and draw structures for A, B and C.
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