Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 8, Problem 1LGP
(a) Synthesize (3S, 4R)-3, 4-dibromo-1-cyclohexylpentane (and its enantiomer, since a racemic mixture will be formed) from ethyne, 1-chloro-2-cyclohexylethane, bromomethane, and any other reagents necessary. (Use ethyne, 1-chloro-2-cyclohexylethane, and bromomethane as the sole sources of carbon atoms.) Stan the problem by showing a retrosynthetic analysis. In the process, decide which atoms of the target molecule will come from which acorns of the starting reagents. Also, bear in mind how the stereospecificity of the reactions you employ can be used to achieve the required stereochemical form of the final product.
(b) Explain why a racemic mixture of products results from this synthesis.
(c) How could the synthesis be modified to produce a racemic mixture of the
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Using reaction free energy to predict equilibrium composition
Consider the following equilibrium:
2NOCI (g) 2NO (g) + Cl2 (g) AGº =41. kJ
Now suppose a reaction vessel is filled with 4.50 atm of nitrosyl chloride (NOCI) and 6.38 atm of chlorine (C12) at 212. °C. Answer the following questions
about this system:
?
rise
Under these conditions, will the pressure of NOCI tend to rise or fall?
x10
fall
Is it possible to reverse this tendency by adding NO?
In other words, if you said the pressure of NOCI will tend to rise, can that
be changed to a tendency to fall by adding NO? Similarly, if you said the
pressure of NOCI will tend to fall, can that be changed to a tendency to
rise by adding NO?
yes
no
If you said the tendency can be reversed in the second question, calculate
the minimum pressure of NO needed to reverse it.
Round your answer to 2 significant digits.
0.035 atm
✓
G
00.
18
Ar
Highlight each glycosidic bond in the molecule below. Then answer the questions in the table under the drawing area.
HO-
HO-
-0
OH
OH
HO
NG
HO-
HO-
OH
OH
OH
OH
NG
OH
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+
Suppose the molecule in the drawing area below were reacted with H₂ over a platinum catalyst. Edit the molecule to show what would happen to it. That is, turn
it into the product of the reaction.
Also, write the name of the product molecule under the drawing area.
Name: ☐
H
C=0
X
H-
OH
HO-
H
HO-
-H
CH₂OH
×
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