Chapter7 - Organic Chemistry CHE 275 Chapter 7...

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Organic Chemistry CHE 275 Chapter 7 Stereochemistry
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A molecule is chiral if its two mirror image forms are not superimposable upon one another. • A molecule is achiral if its two mirror image forms are superimposable. Chirality
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It cannot be superimposed point for point on its mirror image. Bromochlorofluoromethane is Chiral
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To show nonsuperimposability, rotate this model 180° around a vertical axis. Bromochlorofluoromethane is Chiral
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Bromochlorofluoromethane is Chiral
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Another Look
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are enantiomers with respect to each other and nonsuperimposable mirror images are called enantiomers Enantiomers
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Isomers stereoisomers constitutional isomers diastereomers enantiomers
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Chlorodifluoromethane is Achiral
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The two structures are mirror images, but are not enantiomers, because they can be superimposed on each other. Chlorodifluoromethane is Achiral
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a carbon atom with four different groups attached to it also called: chiral center asymmetric center stereocenter stereogenic center w x y z C The Chirality Center
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A molecule with a single chirality center is chiral. Bromochlorofluoromethane is an example. Cl F Br H C Chirality and Chirality Centers
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A molecule with a single chirality center is chiral. 2-Butanol is another example. CH 3 OH H C CH 2 CH 3 Chirality and Chirality Centers
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CH 3 C CH 2 CH 3 CH 2 CH 2 CH 2 CH 3 CH 3 CH 2 CH 2 a chiral alkane One Chirality Center
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Linalool, a naturally occurring chiral alcohol OH One Chirality Center
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1,2-Epoxypropane: a chirality center can be part of a ring O H 2 C CHCH 3 attached to the chirality center are: —H —CH 3 —OCH 2 —CH 2 O One Chirality Center
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Limonene: a chirality center can be part of a ring CH 3 H C CH 3 CH 2 attached to the chirality center are: —H —CH 2 CH 2 —CH 2 CH= —C= One Chirality Center
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Chiral as a result of isotopic substitution CH 3 C D T H One Chirality Center
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A molecule with a single chirality center must be chiral. But, a molecule with two or more chirality centers may be chiral or it may not (Sections 7.10-7.14).
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Symmetry tests for achiral structures Any molecule with a plane of symmetry or a center of symmetry must be achiral .
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A plane of symmetry bisects a molecule into two mirror image halves. Chlorodifluoromethane has a plane of symmetry. A Plane of Symmetry
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Plane of Symmetry The plane has the same thing on both sides for the flask • There is no mirror plane for a hand • We can apply this same analysis to molecules
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A plane of symmetry bisects a molecule into two mirror image halves. 1-Bromo-1-chloro-2-fluoroethene has a plane of symmetry. A Plane of Symmetry
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A substance is optically active if it rotates the plane of polarized light. In order for a substance to exhibit optical activity, it must be chiral and one enantiomer must be present in excess of the other.
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Chapter7 - Organic Chemistry CHE 275 Chapter 7...