EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
6th Edition
ISBN: 9781305687875
Author: Gilbert
Publisher: CENGAGE LEARNING - CONSIGNMENT
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Question
Chapter 7.2, Problem 2E
Interpretation Introduction
Interpretation:
The internal plane of symmetry needs to be represented in the cis-1, 2-cyclohexanediol structure using a dashed line.
Concept Introduction :
Ameso compound is defined as a compound having two or more stereocenterwith an internal plane of symmetry.
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3. How many planes of symmetry does a benzene molecule possess? Which chloro- substituted
16-n
benzene of formula CH₂Clá-n has exactly four planes of symmetry? Draw this isomer and
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7. a) Identify all the chiral/stereogenic centres in the following molecules. Circle the chiral
carbon(s).
OH
CI
-Br
CI
ОН
O,N
CI
Br
CI
CI
A
B
OH
HO,
.CI
Br
HO
OH
b) For each chiral center, prioritize the groups (1-4) attached to each chiral center(s)
Based on your priorities, assign R or S configurations to the chiral center(s).
i)
Но
ii)
H2N H
ОН
но
OH
iv)
OH
OH
v)
H,N-
ČH,OH
Draw the most stable chair conformation for each of the following cyclohexanes.
Now, "flip" the ring and redraw the molecule in the higher energy form.
i) chlorocyclohexane
ii) cis-1-chloro-2-methylcyclohexane
iii) trans-1-methyl-3-propylcyclohexane
9) Below is a statin, simvastatin, used for treating high cholesterol. Assign the stereochemical configuration of
the selected tetrahedral carbon chiral centers (R, S or N (not a chiral center)) and the alkene (E, Z or N (not a
stereocenter)) that are indicated by the arrows (note that you do not have to assign the configuration of every
chiral center in the molecule). If the atom in question is not a chiral center or is not a stereocenter circle N for
neither.
RS N
RS N
HO
RS N
I
RS N
RS N
RS N
EZ N
EZ N
Chapter 7 Solutions
EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
Ch. 7.2 - Prob. 1ECh. 7.2 - Prob. 2ECh. 7.2 - Prob. 3ECh. 7.2 - Prob. 4ECh. 7.2 - Prob. 5ECh. 7.2 - Prob. 6ECh. 7.2 - Prob. 7ECh. 7.2 - Prob. 8ECh. 7.2 - Prob. 9ECh. 7.2 - Prob. 10E
Ch. 7.3 - Prob. 1ECh. 7.3 - Prob. 2ECh. 7.3 - Prob. 3ECh. 7.3 - Prob. 4ECh. 7.3 - Prob. 5ECh. 7.3 - Prob. 6ECh. 7.3 - Prob. 7ECh. 7.3 - Prob. 8ECh. 7.4 - Prob. 1ECh. 7.4 - Prob. 2ECh. 7.4 - Prob. 3ECh. 7.4 - Prob. 4ECh. 7.4 - Prob. 5ECh. 7.4 - Prob. 6ECh. 7.4 - Prob. 7ECh. 7.4 - Prob. 8ECh. 7.4 - Prob. 9ECh. 7.4 - Prob. 10ECh. 7.4 - Prob. 11ECh. 7.4 - Prob. 12ECh. 7.4 - Prob. 13ECh. 7.6 - Prob. 1ECh. 7.6 - Prob. 2ECh. 7.6 - Prob. 3ECh. 7.6 - Prob. 4ECh. 7.6 - Prob. 5ECh. 7.6 - Prob. 6ECh. 7.6 - Prob. 7ECh. 7.6 - Prob. 8ECh. 7.6 - Prob. 9ECh. 7.6 - Prob. 10E
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