Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
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.)
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
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
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.
Threonine has two asymmetric centers and, therefore, has four stereoisomers. Naturally occurring l-threonine is (2S,3R)-threonine. Which of the following stereoisomers is l-threonine?
Chapter 3 Solutions
Organic Chemistry, Loose-leaf Version
Ch. 3.2 - Prob. 3.1PCh. 3.3 - Assign priorities to the groups in each set. (a)...Ch. 3.3 - Prob. 3.3PCh. 3.4 - Following are stereorepresentations for the four...Ch. 3.4 - Prob. 3.5PCh. 3.4 - Prob. 3.6PCh. 3.5 - How many stereoisomers exist for...Ch. 3.5 - How many stereoisomers exist for...Ch. 3.7 - Prob. 3.9PCh. 3.7 - Prob. 3.10P
Ch. 3.8 - If the side chain of the amino add is a methyl...Ch. 3.8 - Prob. BQCh. 3.8 - The amino acids cysteine and serine are shown....Ch. 3.8 - Prob. DQCh. 3.8 - As stated, proteins are stereochemically pure...Ch. 3.8 - As stated, proteins are stereochemically pure...Ch. 3 - Prob. 3.11PCh. 3 - One reason we can be sure that sp3-hybridized...Ch. 3 - Which compounds contain chiral centers? (a)...Ch. 3 - Prob. 3.15PCh. 3 - Prob. 3.16PCh. 3 - Prob. 3.17PCh. 3 - Mark each chiral center in the following molecules...Ch. 3 - Prob. 3.19PCh. 3 - Assign priorities to the groups in each set. (a) H...Ch. 3 - Following are structural formulas for the...Ch. 3 - Following is a staggered conformation for one of...Ch. 3 - Prob. 3.23PCh. 3 - When oxaloacetic acid and acetyl-coenzyme A...Ch. 3 - Prob. 3.25PCh. 3 - Mark each chiral center in the following molecules...Ch. 3 - Prob. 3.27PCh. 3 - Prob. 3.28PCh. 3 - Prob. 3.29PCh. 3 - Prob. 3.30PCh. 3 - Which of the following are meso compounds?Ch. 3 - Prob. 3.32PCh. 3 - Prob. 3.33PCh. 3 - Which of the following compounds are chiral?...Ch. 3 - Prob. 3.35PCh. 3 - Prob. 3.36PCh. 3 - Prob. 3.37PCh. 3 - The chiral catalyst (R)-BINAP-Ru is used to...Ch. 3 - Prob. 3.39P
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- The first step in the metabolism of glycerol, formed by digestion of fats, is phosphorylation of the pro-R—CH2OH group by reaction with adenosine triphosphate (ATP) to give the corresponding glycerol phosphate plus adenosine diphosphate (ADP). Show the stereochemistry of the product.arrow_forwardTreatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). In these representations, the six-membered rings are drawn as planar hexagons. (a) Propose a mechanism for this conversion and account for the fact that only the OH on carbon 1 is transformed into an OCH3 group. (b) Draw the more stable chair conformation for each product. (c) Which of the two products has the chair conformation of greater stability? Explain.arrow_forwardFollowing is a retrosynthesis for the coronary vasodilator ganglefene. (a) Propose a synthesis for ganglefene from 4-hydroxybenzoic acid and 3-methyl-3-buten-2-one. (b) Is ganglefene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forward
- The lactic acid that builds up in tired muscles is formed from pyruvate. If the reaction occurs with addition of hydrogen to the Re face of pyruvate, what is the stereochemistry of the product?arrow_forwardOne of the following molecules (a)–(d) is d-erythrose 4-phosphate, an intermediate in the Calvin photosynthetic cycle by which plants incorporate CO2 into carbohydrates. If d-erythrose 4-phosphate has R stereochemistry at both chirality centers, which of the structures is it? Which of the remaining three structures is the enantiomer of d-erythrose 4-phosphate, and which are diastereomers?arrow_forwardAn acid–base reaction of (R)-sec-butylamine with a racemic mixture of 2-phenylpropanoic acid forms two products having different melting pointsand somewhat different solubilities. Draw the structure of these twoproducts. Assign R and S to any stereogenic centers in the products.How are the two products related? Choose from enantiomers,diastereomers, constitutional isomers, or not isomers of each other.arrow_forward
- Threonine has two asymmetric centers and, therefore, has four stereoisomers. Naturally occurring l-threonine is (2S,3R)-threonine. Which of the following stereoisomers is l-threonine?arrow_forwardCitrate synthase, one of the enzymes in the series of enzyme-catalyzed reactions known as the citric acid cycle, catalyzes the synthesis of citric acid from oxaloacetic acid and acetyl-CoA. If the synthesis is carried out with acetyl-CoA that contains radioactive carbon (14C) in the indicated position , the isomer shown here is obtained. a. Which stereoisomer of citric acid is synthesized: R or S? b. If the acetyl-CoA used in the synthesis contains 12C instead of 14C, will the product of the reaction be chiral or achiral?arrow_forwardHow many stereoisomers are generated by the reaction below? (1) Hg(OAc)2, H20/THF (2) NABH/ethanol Oa pair of enantiomers Oa single stereoisomer a pair of diastereomers four stereoisomersarrow_forward
- Consider the following compound: Given that syn addition of I, occurs from both sides of a trigonal planar double bond, draw all stereoisomers formed when the compound shown is treated with H, in the presence of Pd - C.arrow_forwardCompounds with a d10 configuration will not undergo a reductive elimination reaction, why?arrow_forwardIs compound F produced in this synthesis as a single enantiomer or as a racemic mixture? Explain.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Enzymes - Effect of cofactors on enzyme; Author: Tutorials Point (India) Ltd;https://www.youtube.com/watch?v=AkAbIwxyUs4;License: Standard YouTube License, CC-BY
Enzyme Catalysis Part-I; Author: NPTEL-NOC IITM;https://www.youtube.com/watch?v=aZE740JWZuQ;License: Standard Youtube License