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chapter13_part3

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

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Unformatted text preview: 13-13-1Stereochemistry & TopicityStereochemistry & Topicity◆Depending on the symmetry of a molecule, otherwise equivalent hydrogens may be•homotopic•enantiotopic•diastereotopic◆The simplest way to visualize topicity is to substitute an atom or group by an isotope; is the resulting compound•the same as its mirror image•different from its mirror image•are diastereomers possible13-13-2Stereochemistry & TopicityStereochemistry & Topicity◆Homotopic atoms or groups•homotopic 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 & Topicity◆Enantiotopic groups•enantiotopic atoms or groups have identical chemical shifts in achiral environments•they 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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chapter13_part3 - 13-13-1Stereochemistry& &...

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