Organic Chemistry Fourth Edition - ChemConnections：有机化学第四版- chemconnections.ppt

Molecules with more than OneChiral Carbon 2,3-Dihydroxybutanoic acid What are all the possible R and S combinations of the two chiral carbons in this molecule? 2,3-Dihydroxybutanoic acid 4 Combinations = 4 Stereoisomers 2,3-Dihydroxybutanoic acid 4 Combinations = 4 Stereoisomers What is the relationship between these stereoisomers? 2,3-Dihydroxybutanoic acid 2,3-Dihydroxybutanoic acid stereoisomers that are not enantiomers are diastereomers Fischer Projections recall for Fischer projection: horizontal bonds point toward you; vertical bonds point away staggered conformation does not have correct orientation of bonds for Fischer projection transform molecule to eclipsed conformation in order to construct Fischer projection Erythro and Threo stereochemical prefixes used to specify relative configuration in molecules with two chiral carbons easiest to apply using Fischer projections orientation: vertical carbon chain Erythro when carbon chain is vertical, same (or analogous) substituents on same side of Fischer projection Threo when carbon chain is vertical, same (or analogous) substituents on opposite sides of Fischer projection Achiral MoleculeswithTwo Chiral Centers It is possible for a molecule to have chiral carbons yet be achiral. Any molecule with a plane of symmetryor a center of symmetry must be achiral. Plane of symmetry A plane of symmetry bisects a molecule into two mirror image halves. Chlorodifluoromethane has a plane of symmetry. Plane of symmetry A plane of symmetry bisects a molecule into two mirror image halves. Chlorodifluoromethane has a plane of symmetry. Plane of symmetry A plane of symmetry bisects a molecule into two mirror image halves.1-Bromo-1-chloro-2-fluoroethene has a planeof symmetry. Plane of symmetry A plane of symmetry bisects a molecule into two mirror image halves.1-Bromo-1-chloro-2-fluoroethene has a planeof symmetry. Center of symmetry A point in the center of themolecule is a center of symm