Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Question
Chapter 3, Problem 3.32P
Interpretation Introduction
Interpretation:
Dicarboxylic acid obtained from the given reaction, is an enantiomer, a racemic mixture or a meso compound has to be identified.
Concept Introduction:
Enantiomers:
Stereoisomers having nonsuperposable mirror image relationship are called as enantiomers.
Meso compound:
It is an achiral compound having two or more chiral centers that also has chiral isomers.
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Students have asked these similar questions
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. Does the product have any asymmetric carbon atoms or other stereocenters?
When carbonyl compounds are reduced with a reagent such as LiAlH4 or NaBH4 and a new stereogenic center is formed, what will the composition of the product mixture be?
Forms more of one enantiomer than another because of steric reasons around the carbonyl
Forms more of one enantiomer than another depending on the temperature of the reaction
Forms different products depending on the solvent used
Forms a racemic mixture of the two possible enantiomers
The synthesis of carbohydrates can be particularly difficult because of the large number of chiral centers and OH functional groups present.
Epoxides can be useful synthetic intermediates in carbohydrate synthesis. Draw the product of the reaction of a phenyl Gilman reagent with this
epoxide.
Aa
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
Explicitly define the cis/trans stereochemistry of fused rings using wedge or hash bonds.
If enantiomers are formed, draw both.
Separate multiple products using the sign from the drop-down menu.
.
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
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