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CHEM 212 Lecture 7

CHEM 212 Lecture 7 - ORGANIC CHEMISTRY 212 Lecture 7...

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ORGANIC CHEMISTRY 212 Lecture 7 : September 22 nd , 2009 Youla S. TSANTRIZOS Office: Chemistry Department Pulp & Paper, Room 108 Email: [email protected]
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ORGANIC CHEMISTRY 212 Chapter 5: Stereochemistry - Biological Significance - Isomers and Stereoisomers - Enantiomers
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Resolution of Enantiomers Developed the germ theory created the first vaccine for rabies Developed the process now known as “Pasteurization” to prevent milk and wine from spoiling Resolved tartaric acid from wine (1849) Louis Pasteur (1822 – 1895) French Chemist and Microbiologist by physically separating the crystals of sodium ammonium tartrate
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Enantiomers of Thalidomide N NH O O O O H
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The Cahn-Ingold-Prelog Convention Assign priority based on atomic number Place the substituent of lowest priority to the back CH 3 H 3 R Br Cl If the priority numbering moves clockwise the enantiomer is R If the priority numbering moves counterclockwise enantiomer is S 1 2
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Chirality - Greek word for “handed”
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Chirality H H H H H Cl H H H Cl cis -1,2-dichlorocyclopentane is NOT a chiral compound
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Chirality trans -1,2-dichlorocyclopentane is a chiral compound Enantiomers are nonsuperimposable mirror images
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Asymmetric Carbons: Chiral Centers 2 counterclockwise N C C 1 2 3 3H 3O 1 3 Natural ( S )-Alanine
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Asymmetric Carbons: Chiral Centers 2 counterclockwise 2 clockwise 1 3 Natural ( S )-Alanine Unnatural ( R )-Alanine 1 3
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Priority Assignment for Multiple Bonds C O HO C O HO O C
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Draw the Enantiomers of the Following Compound CH 2 CH 2 Br BrH 2 CH 2 C
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