columbia大学有机化学课件 （三十二）.pptVIP

Chapter 7Stereochemistry 7.1Molecular Chirality: Enantiomers Chirality A molecule is chiral if its two mirror image forms are not superposable upon one another.  A molecule is achiral if its two mirror image forms are superposable. Bromochlorofluoromethane is chiral It cannot be superposed point for point on its mirror image. Bromochlorofluoromethane is chiral To show nonsuperposability, rotate this model 180° around a vertical axis. Bromochlorofluoromethane is chiral Another look Enantiomers are enantiomers with respect to each other Chlorodifluoromethaneis achiral Chlorodifluoromethaneis achiral The two structures are mirror images, but are not enantiomers, because they can be superposed on each other. 7.2The Stereogenic Center The Stereogenic Center a carbon atom with fourdifferent groups attached to it also called: chiral centerasymmetric centerstereocenter Chirality and stereogenic centers A molecule with a single stereogenic center is chiral. Bromochlorofluoromethane is an example. Chirality and stereogenic centers A molecule with a single stereogenic center is chiral. 2-Butanol is another example. Examples of molecules with 1 stereogenic center Examples of molecules with 1 stereogenic center Examples of molecules with 1 stereogenic center attached to the stereogenic center are: —H —CH3 —OCH2 —CH2O Examples of molecules with 1 stereogenic center attached to thestereogenic center are: —H —CH2CH2 —CH2CH= —C= Examples of molecules with 1 stereogenic center A molecule with a single stereogenic centermust be chiral. But, a molecule with two or more stereogenic centers may be chiral or it may not (Sections 7.10-7.13). Symmetry tests for achiral structures 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 tw