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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Question
Chapter 3.7, Problem 3.10P
(a)
Interpretation Introduction
Interpretation:
The configuration for an enantiomer of naproxen has to be assigned.
Concept Introduction:
Priority rules:
- Priorities based on
atomic number
- When priority cannot be assigned on the basis of the atoms bonded directly to the chiral center
- Atoms participating in a double or triple bond are considered to be bonded to an equivalent number of phantom atoms.
For example,
- Priority assignment is made at the first point of difference between groups (should not be based on the larger group).
(b)
Interpretation Introduction
Interpretation:
The percentage of R and S enantiomers in the mixture has to be given.
Concept Introduction:
Enantiomeric excess:
It is the difference betweenthe percentages of twoenantiomers in a given mixture.
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Coibacin B (shown below) is a natural product that exhibits potent anti-inflammatory activity and potential activity in the treatment of leishmaniasis, a disease caused by certain
parasites
(Org. Lett. 2012, 14, 3878-3881):
(a) Assign the configuration (R or S) of each chirality center (labeled A to C) in coibacin B.
(b) Identify the number of possible stereoisomers for this compound, assuming that the geometry of the alkenes are fixed. Choices are given below and write the CAPITAL
LETTER of your choice.
A. 2
В. 4
С. 8
D.
16
ANSWERS:
(a) A.
В.
C.
(b)
5-Hydroxyhexanal forms a six-membered cyclic hemiacetal, which predominates at equilibrium in aqueous solution.
(a) Draw a structural formula for this cyclic hemiacetal.
(b) How many stereoisomers are possible for 5-hydroxyhexanal?
(c) How many stereoisomers are possible for this cyclic hemiacetal?
(d) Draw alternative chair conformations for each stereoisomer and label groups axial or Also predict which of the alternative chair conformations for each stereoisomer is more stable.
How many stereocenters are present in isopulegol? How many stereoisomers are possible for a molecule with this number of stereocenters?
Chapter 3 Solutions
Organic Chemistry
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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