Chapter 5 Chirality and Stereo Chemistry(1).pptx - • 5.2...

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• 5.2 The two major classes of isomers •5.3Looking glass chemistry—Chiral and achiral molecules •5.4Stereogenic centers •5.5Stereogenic centers in cyclic compounds •5.6Labeling stereogenic centers with R or S •5.7Diastereomers •5.8Meso compounds •5.9 R and S assignments in compounds with two or more stereogenic centers •5.10Disubstituted cycloalkanes •5.11Isomers—A summary •5.12Physical properties of stereoisomers •5.13Chemical properties of enantiomers
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Chiral or Achiral? - from Greek for hand
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Pasteur’s Crystals
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Chiral or Achiral?
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Enantiomers are mirror images that are not superimposable A molecule that is not superimposable on its mirror image is a chiral molecule. “Pronounced Kiral” A carbon atom surrounded by four different groups is a chirality center. Other terms in common use are chiral center, chiral carbon, asymmetric carbon, and stereogenic center
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Practice: find the chiral centers
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Thalidomide- a tragic stereochemical story R(+) Thalidomide = S(-) Thaolidomide =
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Prescribed world-wide during the 1950’s and 60’s, Thalidomide was never approved for use in the United States due to the diligence of Frances Oldham Kelsey , a medical reviewing officer for the Food and Drug Administration, who insisted that the safety data on thalidomide were inadequate. Thalidomide manufacturer issues apology – 50 years later September 1, 2012
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Mechanism for Stereospecificity One enantiomer of the amino acid phenylalanine, labeled A, has three groups that can interact with the appropriate binding sites of the chiral receptor. The groups around the chirality center in the mirror image B, however, can never be arranged so that all three groups can bind to these same three binding sites. Thus, enantiomer B does not “fit” the same receptor, so it does not evoke the same response.
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