Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 5.9B, Problem 5.15P
Draw three-dimensional representations of the following compounds. Which have asymmetric carbon atoms'? Which have no asymmetric carbons but are chiral anyway? Use your models for parts (a) through (d) and any others that seem unclear.
- a. CIHC=C=CHCI 1,3dichioroprop8diene
- b. CIHC=C=CHCH3 1-chlorobuta-1,2-diene
- c. CIHC=C=C(CH3) 1-chloro-3-methy1buta-1,2-diene
- d. CIHC=CH—CH=CH2 1-chlorobuta-1,3-diene
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Consider the Newman projections, A-C.
CHO
Н.
H
CHO
OH
A
CH₂OH
OH
но.
н
H
ОН
CH₂OH
B
н.
НО
CHO
OH
C
.CH₂OH
н
i. Determine the structural relationship of A and B; B and C.
ii. Without a change in conformation, assign the configuration to the chiral centers in B.
5. What are the structures of A, B, and C?
NBS
NaOCH2CH 3
A
B
hv
CH3CH,OH, 4
CHO
CH2=CHCO,H
1. 03
2. S(CH3)2
HO2C
CHO
Draw a structural formula of the S configuration of the compound shown below.
• Use the wedge /hash bond tools to indicate stereochemistry where it exists.
Include H atoms at chiral centers only.
• Ifa group is achiral, do not use wedged or hashed bonds on it.
CH3
CH3
CH;CHCHCN
CH,CH,CH,CHCH,CH,
CH2NH2
Draw a structural formula of the RS configuration of the compound shown below.
Use the wedge /hash bond tools to indicate stereochemistry where it exists.
• Include H atoms at chiral centers only.
If a group is achiral, do not use wedged or hashed bonds on it.
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Chapter 5 Solutions
Organic Chemistry (9th Edition)
Ch. 5.2 - Determine whether the following objects are chiral...Ch. 5.2A - Prob. 5.2PCh. 5.2B - Prob. 5.3PCh. 5.2B - Prob. 5.4PCh. 5.2C - Prob. 5.5PCh. 5.3 - Prob. 5.6PCh. 5.3 - Prob. 5.7PCh. 5.4D - Prob. 5.8PCh. 5.4D - Prob. 5.9PCh. 5.4D - Prob. 5.10P
Ch. 5.5 - Prob. 5.11PCh. 5.7 - When optically pure (R)-2-bromobutane is heated...Ch. 5.7 - Prob. 5.13PCh. 5.8 - Prob. 5.14PCh. 5.9B - Draw three-dimensional representations of the...Ch. 5.10A - For each sot of examples, make a model of the...Ch. 5.10A - Draw a Fischer projection for each compound....Ch. 5.10B - Prob. 5.18PCh. 5.10C - For each Fischer projection, label each asymmetric...Ch. 5.11C - Prob. 5.20PCh. 5.13 - Prob. 5.21PCh. 5.13 - Prob. 5.22PCh. 5.15 - Prob. 5.23PCh. 5.16A - Prob. 5.24PCh. 5 - The following four structures are naturally...Ch. 5 - For each structure, 1. star () any asymmetric...Ch. 5 - Prob. 5.27SPCh. 5 - Prob. 5.28SPCh. 5 - Prob. 5.29SPCh. 5 - Prob. 5.30SPCh. 5 - Prob. 5.31SPCh. 5 - Prob. 5.32SPCh. 5 - Prob. 5.33SPCh. 5 - Prob. 5.34SPCh. 5 - For each structure, 1. draw all the stereoisomers....Ch. 5 - Prob. 5.36SPCh. 5 - Prob. 5.37SPCh. 5 - 3,4-Dimethylpent-1-ene has the formula...Ch. 5 - A graduate student was studying enzymatic...Ch. 5 - Prob. 5.40SPCh. 5 - Prob. 5.41SP
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