Organic Chemistry 353-Chapter 5

Organic Chemistry 353-Chapter 5 - Stereochemistry...

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Stereochemistry Stereoisomers
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Chirality ± A chiral object is on that possesses the property of handedness ± Most molecules of life are chiral and are usually found in only one mirror age form image form
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Chirality and Enantiomerism Look for 4 different groups attached to a carbon Nonsuperimposable on its irror image mirror image
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Plane of Symmetry
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Tests for Chirality lane of symmetry ± Plane of symmetry
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Chirality and Enantiomerism ± Asymmetric carbon atom/stereogenic center
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Finding Stereogenic Centers Look for 4 different groups attached to a carbon Cannot be stereogenic centers CH 2 and CH 3 groups Any sp or sp 2 hybridized C
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Practice Finding Stereogenic Centers
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Drawing a Pair of Enantiomers
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Cyclic Compounds
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Nomenclature of Enantiomers: The R,S System eed to be able to distinguish between the two enantiomers ± Need to be able to distinguish between the two enantiomers ± Corn Ingold Prelog system R (from rectus ) S (from sinister ) ± The four groups attached to the stereogenic carbon are assigned priorities from highest (1) to lowest (4) ± Priorities are based on atomic number (i.e. O before C) If atom is same then assign priority on first point of difference I > Br > Cl > S > F > O > N > 13 C > 12 C > Li > 2 H > 1 H
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Cahn Ingold Prelog
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Multiple Bonds
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This note was uploaded on 02/02/2011 for the course CHEM 353 taught by Professor Walsh during the Spring '11 term at University of Evansville.

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Organic Chemistry 353-Chapter 5 - Stereochemistry...

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