Chapter 5 handouts

Chapter 5 handouts - Chapter 5 Stereochemistry Chirality...

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Chapter 5 Stereochemistry
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Chapter 5 2 Chirality • “Handedness”: right glove doesn’t fit the left hand. • Mirror-image object is different from the original object.
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Chapter 5 3 Stereoisomers • __________________: cis-trans isomers. • ______________: nonsuperimposable mirror images, different molecules. cis -1,2-dichlorocyclopentane trans - 1,2-dichlorocyclopentane H Cl H H H H H H H
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Chapter 5 4 Chiral Carbons • __________ carbons with 4 different attached groups are _______. (stereogenic center) • Its mirror image will be a different compound (__________).
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Chapter 5 5 Mirror Planes of Symmetry If two groups are the same, carbon is __________. A molecule with an internal ________ ________ cannot be chiral.* *Caution! If there is no plane of symmetry, molecule may be chiral or achiral. See if mirror image can be superimposed.
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Chapter 5 6 ( R ), ( S ) Nomenclature • Different molecules (enantiomers) must have different _______. • Usually only one enantiomer will be _______________. • ____________ around the chiral carbon is specified with ( R ) and ( S ). C C O OH H 3 C NH 2 H natural alanine =>
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Chapter 5 7 Cahn-Ingold-Prelog Rules • Assign a _____________ to each group attached to the chiral carbon. • Atom with ________ atomic number assigned the ________ priority #1. • In case of ties, look at the ________ along the chain. • Double and triple bonds are treated like bonds to _____________.
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Chapter 5 8 Assign Priorities C C O OH H 3 C NH 2 H natural alanine Cl H H * C C O H C H CH 2 2 CH(CH 3 ) 2 * C C C 2 3 ) 2 H O O C C HC H 2 C * expands to
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Chapter 5 9 Assign ( R ) or ( S ) • Working in 3D, rotate molecule so that _______ priority group is in back.
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This note was uploaded on 04/08/2008 for the course CHEM 223 taught by Professor Pearson during the Fall '07 term at Case Western.

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Chapter 5 handouts - Chapter 5 Stereochemistry Chirality...

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