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.
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H
ОН
CH₂OH
B
н.
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CHO
OH
C
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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.
Two structures are shown. Identify the asymmetric carbons in each structure, classify as chiral or achiral, and identify the
number of stereocenter(s).
H.
„CH3
H3C
CH3
H
H.
CH3
compound A
compound B
Which image shows the asymmetric carbon(s) in compound A highlighted in red?
CI
H
H3C
CH3
H,C
CH3
O Neither. There are no asymmetric carbons in compound A.
H.
H3C
-CH3
C
H3C
CH3
Compound A is
. There are
stereocenters in compound A.
Which image shows the asymmetric carbon(s) in compound B highlighted in reď?
.CH3
H
H.
CH3
H3C.C
H
O Neither. There are no asymmetric carbons in compound B.
Compound B is
There are
stercocenters in compound B.
*Please explain all the
questions
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Question 4
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Which molecule is the enantiomer of this molecule?
H.
H3C
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CICH,
CH3
Bri C H
CH,CI
CH,CI
Br C-H
CH3
H3C
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CICH, H
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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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