just problem 5.20 please

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter7: Cycloalkanes
Section: Chapter Questions
Problem 17E: Build a model of methylcyclohexane, and use the model to complete the following Newmanprojections of...
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just problem 5.20 please
present a pair of enantiomers. Formulas Cand D represent identical orientations of the
Br H
H
Br
ures A and B are nonsuperposable and represent a pair of enantiomers.
a we write the new structure C (see below) and its mirror image D, however, the
a is different. The two structures are superposable. This means that C and D do not
sume compound:
H H
H H
Br
Br
Br
Br
C
D
The molecule represented by structure C (or D) is not chiral even though it contains
Wo chirality centers.
• If a molecule has an internal plane of symmetry it is achiral.
A meso compound is an achiral molecule that contains chirality centers and has an
internal plane of symmetry. Meso compounds are not optically active.
Another test for molecular chirality is to construct a model (or write the structure) of
the molecule and then test whether or not the model (or structure) is superposable on its
mirror image. If it is, the molecule is achiral. If it is not, the molecule is chiral.
We have already carried out this test with structure C and found that it is achiral. We dibromobutane. This plane
can also demonstrate that C is achiral in another way. Figure 5.15 shows that structure C
has an internal plane of rymmetry (Section 5.6).
The following two problems relate to compounds A-D in the preceding paragraphs.
FIGURE 5.15 The plane
of symmetry of meso-2,3-
divides the molecule into halves
that are mirror images of each
other.
Which of the following would be optically active?
•PRACTICE PROBLEM 5.20
(a) A pure sample of A
b) A pure sample of B
(c) A pure sample of C
(d) An equimolar mixture of A and B
Transcribed Image Text:present a pair of enantiomers. Formulas Cand D represent identical orientations of the Br H H Br ures A and B are nonsuperposable and represent a pair of enantiomers. a we write the new structure C (see below) and its mirror image D, however, the a is different. The two structures are superposable. This means that C and D do not sume compound: H H H H Br Br Br Br C D The molecule represented by structure C (or D) is not chiral even though it contains Wo chirality centers. • If a molecule has an internal plane of symmetry it is achiral. A meso compound is an achiral molecule that contains chirality centers and has an internal plane of symmetry. Meso compounds are not optically active. Another test for molecular chirality is to construct a model (or write the structure) of the molecule and then test whether or not the model (or structure) is superposable on its mirror image. If it is, the molecule is achiral. If it is not, the molecule is chiral. We have already carried out this test with structure C and found that it is achiral. We dibromobutane. This plane can also demonstrate that C is achiral in another way. Figure 5.15 shows that structure C has an internal plane of rymmetry (Section 5.6). The following two problems relate to compounds A-D in the preceding paragraphs. FIGURE 5.15 The plane of symmetry of meso-2,3- divides the molecule into halves that are mirror images of each other. Which of the following would be optically active? •PRACTICE PROBLEM 5.20 (a) A pure sample of A b) A pure sample of B (c) A pure sample of C (d) An equimolar mixture of A and B
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