Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 3, Problem 3.24P

When oxaloacetic acid and acetyl-coenzyme A (acetyl-CoA) labeled with radioactive carbon-14 in position 2 are incubated with citrate synthase, an enzyme of the tricarboxylic acid cycle, only the following enantiomer of [2-l4C]citric acid is formed stereoselectively. Note that citric acid containing only 12C is achiral. Assign an R or S configuration to this enantiomer of [2-14C]citric acid. (Note: Carbon-14 has a higher priority than carbon-12.)

Chapter 3, Problem 3.24P, When oxaloacetic acid and acetyl-coenzyme A (acetyl-CoA) labeled with radioactive carbon-14 in

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When oxaloacetic acid and acetyl-coenzyme A (acetyl-CoA) labeled with radioactive carbon-14 in position 2 are incubated with citrate synthase, an enzyme of the tricarboxylic acid cycle, only the following enantiomer of [2-14C]citric acid is formed stereoselectively. Note that citric acid containing only 12C is achiral. Assign an R or S configuration to this enantiomer of [2-14C]citric acid. (Note: Carbon-14 has a higher priority than carbon-12.) C-COOH 14CH,COOH citrate synthase ČH,COOH + 14CH,CSCOA НООС -COH CH,COOH Oxaloacetic acid Acetyl-CoA [2-14C]Citric acid
Clopidogrel is the generic name for Plavix, a drug used to prevent the formation of blood clots in patients that have a history of heart attacks or strokes. A single enantiomer of clopidogrel can be prepared in three steps from the chiral α-hydroxy acid A. Identify B and C in the following reaction sequence, and designate the configuration of the enantiomer formed by this route as R or S.
The following bicyclic ketone has two a-carbons and three a-hydrogens. When this molecule is treated with D,O in the presence of an acid catalyst, only two of the three a-hydrogens exchange with deuterium. The a-hydrogen at the bridgehead does not exchange. H these two a-hydrogens exchange H. this a-hydrogen does not exchange H How do you account for the fact that two a-hydrogens do exchange but the third does not? You will find it helpful to build models of the enols by which exchange of a-hydrogens occurs.

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