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chap5solomons - Chapter5 Stereochemistry ChiralMolecules...

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Created by Professor William Tam & Dr. Phillis Chang Ch. 5 - Chapter 5 Chapter 5 Stereochemistry Stereochemistry Chiral Molecules Chiral Molecules
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About The Authors About The Authors These Powerpoint Lecture Slides were created and prepared by Professor  William Tam and his wife Dr. Phillis Chang.   Professor William Tam received his B.Sc. at the University of Hong Kong in  1990 and his Ph.D. at the University of Toronto (Canada) in 1995.  He was an  NSERC postdoctoral fellow at the Imperial College (UK) and at Harvard  University (USA).  He joined the Department of Chemistry at the University of  Guelph (Ontario, Canada) in 1998 and is currently a Full Professor and  Associate Chair in the department.  Professor Tam has received several  awards in research and teaching, and according to  Essential Science  Indicators , he is currently ranked as the Top 1% most cited Chemists  worldwide.  He has published four books and over 80 scientific papers in top  international journals such as  J. Am. Chem. Soc., Angew. Chem., Org. Lett.,  and  J. Org. Chem.   Dr. Phillis Chang received her B.Sc. at New York University (USA) in 1994, her  M.Sc. and Ph.D. in 1997 and 2001 at the University of Guelph (Canada).  She  lives in Guelph with her husband, William, and their son, Matthew. Ch. 5
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Ch. 5 - 1. Chirality & Stereochemistry An object is  achiral  (not chiral) if the  object and its mirror image are identical
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Ch. 5 - chiral  object is one that cannot be  superposed on its mirror image
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Ch. 5 - 1A. 1A. The Biological Significance of The Biological Significance of Chirality Chirality Chiral molecules are molecules that  cannot be superimposable with their  mirror images Thalidomide N NH O O O O One enantiomer  causes birth  defects, the other  cures morning  sickness
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Ch. 5 - One enantiomer is a bronchodilator, the  other inhibits platelet aggregation NH OMe OMe OMe HO HO Tretoquinol
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Ch. 5 - 66% of all drugs in development are  chiral , 51% are being studied as a  single  enantiomer Of the $475 billion in world-wide sales of  formulated pharmaceutical products in  2008, $205 billion was attributable to  single enantiomer drugs
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Ch. 5 - 1. Isomerisom: Constitutional Isomers & Stereoisomers Isomers : different compounds that  have the same molecular formula Constitutional isomers : isomers  that have the same molecular  formula but different connectivity – their atoms are connected in a  different order 2A.
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