chapter13_part3 - 13-13-1Stereochemistry &...

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Unformatted text preview: 13-13-1Stereochemistry & TopicityStereochemistry & TopicityDepending on the symmetry of a molecule, otherwise equivalent hydrogens may behomotopicenantiotopicdiastereotopicThe simplest way to visualize topicity is to substitute an atom or group by an isotope; is the resulting compoundthe same as its mirror imagedifferent from its mirror imageare diastereomers possible13-13-2Stereochemistry & TopicityStereochemistry & TopicityHomotopic atoms or groupshomotopic atoms or groups have identical chemical shifts under all conditionsAchiralHCHClClHCDClClDichloro-methane(achiral)Substitution does not produce a stereocenter;therefore hydrogensare homotopic.Substitute one H by DAchiralHCHClClHCDClClDichloro-methane(achiral)Substitution does not produce a stereocenter;therefore hydrogensare homotopic.Substitute one H by D13-13-3Stereochemistry & TopicityStereochemistry & TopicityEnantiotopic groupsenantiotopic atoms or groups have identical chemical shifts in achiral environmentsthey have different chemical shifts in chiral environmentsChiralHCHClFHCDClFChlorofluoro-methane(achiral)Substitute one H by DSubstitution produces a stereocenter;therefore, hydrogens are enantiotopic. Both hydrogens are prochiral; one is pro-R-chiral, the other is pro-S-chiral.ChiralHCHClFHCDClFChlorofluoro-methane(achiral)Substitute one H by DSubstitution produces a stereocenter;therefore, hydrogens are enantiotopic. Both hydrogens are prochiral; one is pro-R-chiral, the other is pro-S-chiral.13-13-4Stereochemistry & TopicityStereochemistry & Topicity...
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This note was uploaded on 09/19/2011 for the course CHM 262 taught by Professor Staff during the Spring '08 term at Purdue University-West Lafayette.

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chapter13_part3 - 13-13-1Stereochemistry &...

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