CHEM 212 Lecture 7

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

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Unformatted text preview: ORGANIC CHEMISTRY 212 Lecture 7 : September 22 nd , 2009 Youla S. TSANTRIZOS Office: Chemistry Department Pulp & Paper, Room 108 Email: youla.tsantrizos@mcgill.ca ORGANIC CHEMISTRY 212 Chapter 5: Stereochemistry - Biological Significance omers and tereoisomers- Isomers and Stereoisomers- Enantiomers 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 Louis Pasteur (1822 1895) French Chemist and Microbiologist Resolved tartaric acid from wine (1849) by physically separating the crystals of sodium ammonium tartrate Enantiomers of Thalidomide N NH O O O O H The Cahn-Ingold-Prelog Convention Assign priority based on atomic number Place the substituent of lowest priority to the back CH 3 3 R Br H Cl If the priority numbering moves clockwise the enantiomer is R If the priority numbering moves counterclockwise enantiomer is S 1 2 Chirality - Greek word for handed Chirality H H H H H Cl H H H Cl cis-1,2-dichlorocyclopentane is NOT a chiral compound Chirality trans-1,2-dichlorocyclopentane is a chiral compound Enantiomers are nonsuperimposable mirror images Asymmetric Carbons: Chiral Centers 2 counterclockwise N C C 1 2 3 3H 3O 1 3 Natural ( S )-Alanine Asymmetric Carbons: Chiral Centers 2 counterclockwise 2 clockwise 1 3 Natural ( S )-Alanine Unnatural ( R )-Alanine 1 3 Priority Assignment for Multiple Bonds C O HO C O HO O C Draw the Enantiomers of the Following Compound 2 2 CH 2 CH 2 Br C CH 3 Br H BrH 2 CH 2 C C H 3 C Br H 1 3 1 3 (3 R )-1,3-dibromobutane (3 S )-1,3-dibromobutane Physical Properties of Anantiomers...
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CHEM 212 Lecture 7 - ORGANIC CHEMISTRY 212 Lecture 7 :...

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