Chapter 7 - Chapter Chapter 7 Stereochemistry Chem 211 B R...

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hapter 7 Chapter 7 Stereochemistry Chem 211 B. R. Kaafarani 1
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Chirality A molecule is chiral if its two mirror imagefo rms are not superimposable upon one another. A molecule is achiral if its two mirror image rms re uperimposable forms are superimposable. Chem 211 B. R. Kaafarani 2
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Chem 211 B. R. Kaafarani 3
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Bromochlorofluoromethane is chiral r Cl It cannot be Br H superimposed point for point F on its mirror image. Chem 211 B. R. Kaafarani 4
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Bromochlorofluoromethane is chiral r Cl Cl r Br H H Br F F To To show show nonsuperimposability, nonsuperimposability, rotate rotate this this model model 180 180 ° around around a Chem 211 B. R. Kaafarani 5 vertical vertical axis axis.
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Bromochlorofluoromethane is chiral r Cl Cl Br Br H H F F Chem 211 B. R. Kaafarani 6
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Another look Chem 211 B. R. Kaafarani 7
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Enantiomers nonsuperimposable mirror images are called enantiomers and are enantiomers with respect to each other! Chem 211 B. R. Kaafarani 8
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Isomers ame molecular formula onstitutional same molecular formula stereoisomers constitutional isomers Different connectivity Same Same connectivity connectivity; different arrangement of atoms in space diastereomers enantiomers Chem 211 B. R. Kaafarani 9 Nonsuperimposable mirror images Not enantiomers
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Chlorodifluoromethane is achiral Chem 211 B. R. Kaafarani 10
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Chlorodifluoromethane is achiral The two structures are mirror images, but are not enantiomers, because they can be superimposed on Chem 211 B. R. Kaafarani 11 each other.
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7.2. The Chirality Center A carbon atom with four different w groups attached to it x y C Also called: Chiral center z Asymmetriccenter Stereocenter tereogenic enter Stereogenic center Chem 211 B. R. Kaafarani 12
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Chirality and Chirality Centers A molecule with a single chirality center is chiral . Bromochlorofluoromethane & 2-butanol are examples. H H Cl F C CH 3 C CH 2 CH 3 Br OH CH 3 C CH 2 CH 2 CH 2 CH 3 CH 3 CH 2 CH 2 Chem 211 B. R. Kaafarani 13 CH 2 CH 3 Chiral alkane
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Examples of Molecules With 1 Chirality Center OH Linalool, a naturally occurring chiral alcohol Chem 211 B. R. Kaafarani 14
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Examples of Molecules With 1 Chirality Center H C CHCH O 2 3 1,2-Epoxypropane: chirality center can be part of a ring. Attached to the chirality center are: —H —CH 3 —OCH Chem 211 B. R. Kaafarani 15 2 —CH 2 O
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Examples of Molecules With 1 Chirality Center imonene hirality Limonene: a chirality center can be part of a ring. CH 3 Attached to the H C CH chirality center are: —H CH 3 2 —CH 2 CH 2 —CH 2 CH= Chem 211 B. R. Kaafarani 16 —C=
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Examples of Molecules With 1 Chirality Center H H CH 3 C D T D: Deuterium ( 2 H) T: Tritium ( 3 H) Chiral as a result of isotopic substitution. Chem 211 B. R. Kaafarani 17
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7.3. Symmetry in Achiral Structures A molecule with a single chirality center must be chiral.
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This note was uploaded on 01/06/2012 for the course CHEM 211 taught by Professor Bilalkaafarani during the Spring '11 term at American University of Beirut.