Chapter 5 Stereochemistry 有机化学英文版教学课件（美国达拉斯社区学院） 《Organic Chemistry 5th Edition (L.G. Wade JR.)》.pptVIP

Chapter 5 Chapter 5Stereochemistry Chirality “Handedness”: right glove doesn’t fit the left hand. Mirror-image object is different from the original object. = Stereoisomers Geometric isomers: cis-trans isomers. Enantiomers: nonsuperimposable mirror images, different molecules.  = Chiral Carbons Tetrahedral carbons with 4 different attached groups are chiral. Its mirror image will be a different compound (enantiomer). = Mirror Planes of Symmetry If two groups are the same, carbon is achiral. (animation) A molecule with an internal mirror plane cannot be chiral.* (R), (S) Nomenclature Different molecules (enantiomers) must have different names. Usually only one enantiomer will be biologically active. Configuration around the chiral carbon is specified with (R) and (S). Cahn-Ingold-Prelog Rules Assign a priority number to each group attached to the chiral carbon. Atom with highest atomic number assigned the highest priority #1. In case of ties, look at the next atoms along the chain. Double and triple bonds are treated like bonds to duplicate atoms. = Assign Priorities Assign (R) or (S) Working in 3D, rotate molecule so that lowest priority group is in back. Draw an arrow from highest to lowest priority group. Clockwise = (R), Counterclockwise = (S)  = Properties of Enantiomers Same boiling point, melting point, density Same refractive index Different direction of rotation in polarimeter Different interaction with other chiral molecules Enzymes Taste buds, scent  = Optical Activity Rotation of plane-polarized light Enantiomers rotate light in opposite directions, but same number of degrees.