Wade:organic Chemistrych5

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detailed steriochemical picture of a molecule; the (R) and (S) configuration at each assymetric carbon atom

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absolute configuration

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not chiral; same as its mirror image

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achiral

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a carbon atom that is bonded to four different groups

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asymmetric carbon atom or
chiral carbon atom

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accepted method for designating the absolute configuration of a chirality center ( usually an asymmetric carbon) as either (R) or (S)

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Cahn-Ingold-Prelog convention

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different from its mirror image

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chiral

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the IUPAC term for an atom holding a set of ligands in a spatial arrangement that is not superimposable on its mirror image

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chirality center

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a molecule or object that is chiral and can use its own chiralityto differentiate between mirror images

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chiral probe

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on the same side of a ring or double bond

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cis

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isomers that differ in their geometric arrangement on a ring or double bond; subclass of diastereomers

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cis-trans isomers

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the two possible spatial arrangements around a chirality center or other stereocenter

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configuration

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structures that differ only by rotations about single bonds; interconvert at room temperature and are not true isomers

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conformers or
conformations

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isomers that differ in the order that their atoms are bonded

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constitutional isomers

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rotating the plane of polarized light clockwise (+) or (d)

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dextrorotatory

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stereoisomers that are not mirror images

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diastereomers

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the excess of one enantiomer in a mixture of enantiomers expressed as a percentage of the mixture; similar to optical purity

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enantiomeric excess (e.e.)

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a pair of non-superimposable mirror-image molecules; mirror-image isomers

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enantiomers

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a method of drawing an asymmetric carbon atom as a cross; carbon chain is kept along the vertical; horizontal bonds project toward the viewer

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Fischer projections

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a plane of symmetry through the middle of a molecule, dividing the molecule into two mirror-image halves

* a molecule with an internal mirror plane of symmetry cannot be chiral

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internal mirror plane

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different compounds with the same molecular formula

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isomers

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rotating the plane of polarized light counterclockwise (-) or (l)

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levoratatory

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compounds with identical properties except for the direction in which they rotate polarized light

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optical isomers

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capable of rotating the plane of polarized light

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optically active

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the specific rotation of a mixture of two enatiomers, expressed as a percentage of the specific rotation of one of the pure enantiomers

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optical purity (o.p.)

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light composed of waves that vibrate in only one plane

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plane-polarized light

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an instrument that measures the rotation of plane-polarized light by an optically active compound

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polarimeter

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mixture of equal quantities of enantiomers, such that the mixture is optically inactive

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racemic mixture

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experimentally determined relationship between the configurations of two molecules even when absolute configurations are not known

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relative configuration

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process of separating a racemic mixture into the pure enantiomers

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resolution

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a chiral compound used for separating enantiomers

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resolving agent

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measure of a compounds ability to rotate the plane of polarized light...

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specific rotation

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atom that gives rise to stereoisomers when its groups are interchanged; asymmetric carbon atoms and double-bonded carbons in cis-trans alkenes are the most common

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stereocenter

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study of the three-dimensional structure of molecules

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stereochemistry

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isomers whose atoms are bonded togather in the same order, but they differ in how the atoms are oriented in space

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stereoisomer

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isomers that differ in the order in which their atoms are bonded togather

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structural isomers

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identical in all respects; three-dimensional positions of all atoms coincide when the molecules are placed on top of each other

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superimposable

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opposite sides of a ring or double bond

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trans