Chapter 6 - Chapter 6. Principles of Stereochemistry...

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Unformatted text preview: Chapter 6. Principles of Stereochemistry Chirality OH H C H CH3 ethanol * asymmetric carbon Plane of symmetry If a compound has a plane of symmetry, it is not chiral. Center of Symmetry If a compound has a center of symmetry, it is not chiral. The R ­, S ­ System Op@cal ac@vity of enan@omers Dextrorotatory Levorotatory Stereochemical correla@on The sign of op@cal rota@on is unrelated to the R or S configura@on of the compound. Diastereomers Drawing structures Sawhorse projec@on Line ­and ­wedge structure Meso Compounds (2S, 3S) (2R, 3R) (2S, 3R) (2R, 3S) Racemates and enan@omeric resolu@on Chiral molecules without asymmetric atoms Conforma@onal stereoisomers Asymmetric Nitrogen: amine inversion Key Points •  •  •  •  •  •  •  •  •  Chirality, enan@omers, achiral; Stereocenter, asymmetric carbon carbons; R,S nomenclature; Symmetry elements (plane and center of symmetry); Op@cal ac@vi@es of enan@omers; Racemate, racemiza@on, and enan@omeric resolu@on; Diastereomers and their proper@es; Meso compounds; Compounds with no chiral carbons can be chiral; compounds with chrial carbons can be achiral •  Conforma@onal isomer; •  Newman projec@ons; Sawhorse projec@on; line ­and ­wedge structures; •  Amine inversion. ...
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This note was uploaded on 08/24/2010 for the course CHEM 3351 at Colorado.

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