Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 10, Problem 9PP
Interpretation Introduction
Interpretation:
The stereoisomeric properties of the products of chlorination of
Concept introduction:
Stereoisomers are characterized for the molecules that have same molecular formula and arrangement of atoms but differ in the spatial orientation of groups in the molecule.
Stereoisomers are further divided into enantiomers and diastereomers. Diastereomers are the stereoisomers that are non-superimposable and non-mirror images of each other.
A meso isomer, or the meso compound, is a stereoisomer which has a superimposable mirror image.
A meso compound is optically inactive due to presence internal compensation
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• PRACTICE PROBLEM 6.6 S 2 reactions that involve substitution at a chirality center can be used to relate the
configuration of one molecule to another, because we know the SN2 reaction will occur
with inversion.
(a) Illustrate how this is true by assigning R,S configurations to the 2-chlorobutane
enantiomers based on the following data. [The configuration of (-)-2-butanol is given
in Section 5.8C.]
HO-
(+)-2-Chlorobutane
(-)-2-Butanol
SN2
[a]3 = +36.00
(Enantiomerically pure)
[a] = -13.52
(Enantiomerically pure)
noin
(b) When enantiomerically pure (+)-2-chlorobutane is allowed to react with potassium
iodide in acetone in an SN2 reaction, the 2-iodobutane that is produced has a minus
optical rotation. What is the configuration of (-)-2-iodobutane? Of (+)-2-iodobutane?
Review Problem 5.2
Construct handheld models of the 2-butanols represented in Fig. 5.3 and demonstrate for
yourself that they are not mutually superposable. (a) Make similar models of 2-bromo-
propane. Are they superposable? (b) Is a molecule of 2-bromopropane chiral? (c) Would
you expect to find enantiomeric forms of 2-bromopropane?
H
но
OH H
HO HH OH
OH
HO H
CH
CH
CH
C CH
CH
II
II
(a)
(b)
(c)
Figure 5.3 (a) Three-dimensional drawings of the 2-butanol enantiomers I and II. (b) Models of
the 2-butanol enantiomers. (c) An unsuccessful attempt to superpose models of I and II.
CH3
CH3
2 Predict the stereochemistry of each of the following reactions:
(a)
H3C.
(d)
CH3
LIAIH4
epoxidation
CH2
(е)
KMNO4
(b)
NaBH4
(c)
catalytic
CH3
hydrogenation
Chapter 10 Solutions
Organic Chemistry
Ch. 10 - Prob. 1PPCh. 10 - Prob. 2PPCh. 10 - Practice Problem 10.3 How would the molecular ion...Ch. 10 - Prob. 4PPCh. 10 - Prob. 5PPCh. 10 - Prob. 6PPCh. 10 - Practice Problem 10.7 Chlorination reactions of...Ch. 10 - Prob. 8PPCh. 10 - Prob. 9PPCh. 10 - Prob. 10PP
Ch. 10 - Prob. 11PPCh. 10 - Practice Problem 10.12 Benzylic radicals, due to...Ch. 10 - Prob. 13PPCh. 10 - Practice Problem 10.14 Show how the following...Ch. 10 - Prob. 15PPCh. 10 - Prob. 16PPCh. 10 - Prob. 17PPCh. 10 - Prob. 18PCh. 10 - Explain the relative distribution of produces...Ch. 10 - 10.20 Which of the following compounds can be...Ch. 10 - Prob. 21PCh. 10 - Prob. 22PCh. 10 - Prob. 23PCh. 10 - Prob. 24PCh. 10 - 10.25 List in order of decreasing stability all of...Ch. 10 - Prob. 26PCh. 10 - Prob. 27PCh. 10 - Prob. 28PCh. 10 - Starting with the compound or compounds indicated...Ch. 10 - Prob. 30PCh. 10 - 10.31 Synthesize each of the following compounds...Ch. 10 - 10.32 Synthesize each of the following compounds...Ch. 10 - Prob. 33PCh. 10 - Prob. 34PCh. 10 - Prob. 35PCh. 10 - Write a mechanism for the following reaction.Ch. 10 - Prob. 37PCh. 10 - The halogen atom of an alkyl halide can be...Ch. 10 - Prob. 39PCh. 10 - Prob. 40PCh. 10 - If one were to try to draw the simplest Lewis...Ch. 10 - Prob. 1LGPCh. 10 - 2. (a) Propose a synthesis of 2-methoxypropene...Ch. 10 - Use the single-bond dissociation energies of Table...Ch. 10 - 10.2 In the radical chlorination of methane, one...Ch. 10 - Prob. 3QCh. 10 - Use the single-bond dissociation energies of Table...Ch. 10 - Prob. 5QCh. 10 - Prob. 6Q
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