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09 Ch05 - CHAPTER 5 Stereochemistry The Arrangement of...

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144 CHAPTER 5 Stereochemistry: The Arrangement of Atoms in Space; The Stereochemistry of Addition Reactions Important Terms absolute configuration the three-dimensional structure of a chiral compound. The configuration is designated by R or S . The configuration is called absolute to distinguish it from a relative configuration. achiral a molecule or object that contains an element (a plane or a point) of (optically inactive) symmetry. amine inversion results when a compound containing an sp 3 hybridized nitrogen with a nonbonding pair of electrons rapidly turns inside out. anti addition an addition reaction in which the two added substituents add to opposite sides of the molecule. asymmetric center a atom that is bonded to four different substituents. biochemistry the chemistry associated with living organisms. chiral a chiral molecule has a nonsuperimposable mirror image. (optically active) chiral catalyst a catalyst that will cause the synthesis of one enantiomer in great excess over the other. chiral probe something capable of distinguishing between enantiomers. cis isomer the isomer with substituents on the same side of a cyclic structure, or the isomer with the hydrogens on the same side of a double bond. cis-trans isomers geometric (or E , Z ) isomers. chromatography a separation technique in which the mixture to be separated is dissolved in a solvent and the solution is passed through a column packed with an adsorbent stationary phase. configuration the three-dimensional structure of a chiral compound. The configuration is designated by R or S . configurational isomers stereoisomers that cannot interconvert unless a covalent bond is broken. Cis-trans isomers and optical isomers are configurational isomers. constitutional isomers molecules that have the same molecular formula but differ in the way the (structural isomers) atoms are connected. dextrorotatory the enantiomer that rotates polarized light in a clockwise direction.
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Chapter 5 145 diastereomer a configurational isomer that is not an enantiomer. enantiomers nonsuperimposable mirror-image molecules. enantiomerically pure only one enantiomer is present in an enantiomerically pure sample. enantiomeric excess how much excess of one enantiomer is present in a mixture of a pair of enantiomers. enzyme a protein that catalyzes a biological reaction. erythro enantiomers the pair of enantiomers with similar groups on the same side (in the case of stereoisomers with adjacent asymmetric centers) when drawn in a Fischer projection. Fischer projection a method of representing the spatial arrangement of groups bonded to an asymmetric center. The asymmetric center is the point of intersection of two perpendicular lines; the horizontal lines represent bonds that project out of the plane of the paper toward the viewer, and the vertical lines represent bonds that project back from the plane of the paper away from the viewer.
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