厦门大学化学化工学院：《有机化学》课程教学资源（课件讲稿，双语版）第五章 立体化学：手性分子（5.1-5.7）Isomerism：Constitutional Isomers and Stereoisomers

Chapter 5 Stereochemistry Chiral Molecules 立体化学手性

Chapter 5 Stereochemistry: Chiral Molecules 立体化学: 手性分子

ORGANIC CHEMISTRY Chapter 5 5.isomerism: Constitutional somers and stereoisomers 异构现象:构造异构和立体异构 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 5 5.1 Isomerism: Constitutional Isomers and Stereoisomers 异构现象：构造异构和立体异构

ORGANIC CHEMISTRY Chapter 5 Isomers Isomers are different compounds that have the same molecular formula g Constitutional isomers are isomers that differ because their atoms are connected in a different order g Stereoisomers differ only in arrangement of their atoms in space. Stereoisomers are not constitutional Isomers g Enantiomers are stereoisomers whose molecules are nonsuperposable mirror images of each other. g Diastereomer are stereoisomers whose molecules are not mirror images of each other Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 5 Isomers Isomers are different compounds that have the same molecular formula. Constitutional isomers are isomers that differ because their atoms are connected in a different order. Stereoisomers differ only in arrangement of their atoms in space.Stereoisomers are not constitutional isomers. Enantiomers are stereoisomers whose molecules are nonsuperposable mirror images of each other. Diastereomer are stereoisomers whose molecules are not mirror images of each other

ORGANIC CHEMISTRY Chapter 5 5.2 Enantiomers and chiral molecules 对映异构和手性分子 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 5 5.2 Enantiomers and Chiral molecules 对映异构和手性分子

ORGANIC CHEMISTRY Chapter 5 g Chiral: An object that if it is not superimposable on its mirror image o Chiral molecules:a chiral molecule is defined as one that is not identical with its mirror image o Achiral: Objects that are superposable on their Images are achiral Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 5 Chiral: An object that if it is not superimposable on its mirror image. Chiral molecules: A chiral molecule is defined as one that is not identical with its mirror image. Achiral: Objects that are superposable on their images are achiral

ORGANIC CHEMISTRY Chapter 5 Enantiomers g Molecules that are nonidentical with their mirror images are a special kind of stereoisomers called enantiomers MiTTe Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 5 Enantiomers Molecules that are nonidentical with their mirror images are a special kind of stereoisomers called enantiomers

ORGANIC CHEMISTRY Chapter 5 a pair of enantiomers is al ways possible for molecules that contain one tetrahedral atom with four different groups attached to it o Interchanging any two groups at the tetrahedral atom that bears four different groups converts one enantiomer into the other o Stereocenter-an atom bearing groups of such nature that an interchange of any two groups will produce a stereoisomer Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 5 A pair of enantiomers is always possible for molecules that contain one tetrahedral atom with four different groups attached to it. Interchanging any two groups at the tetrahedral atom that bears four different groups converts one enantiomer into the other. Stereocenter — an atom bearing groups of such nature that an interchange of any two groups will produce a stereoisomer

ORGANIC CHEMISTRY Chapter 5 5.3 The Biological Importance of Chirality Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 5 5.3 The Biological Importance of Chirality

ORGANIC CHEMISTRY Chapter 5 H OH CO,H HO HO H OH-H H NH CHCONH H OH D-Glucose D-Asparagine (+)-D-葡萄糖 D天门冬酰胺 D-form--sweet L-form--bitter Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 5 HO O H H HO H OH H OH H OH (+)-D-葡萄糖 CO2H H NH2 CH2CONH2 D-天门冬酰胺 D-Glucose D-Asparagine D-form—sweet L-form—bitter

ORGANIC CHEMISTRY Chapter 5 NHCOCHCI2 HOCHoCH--CHOH Ph、COCH2CH Pht CH2CHN(CH3) CH NO2 Chloromycetin Methadone 氯霉素 美散痛 (+)-Chloromycentin (+)-Methadone effectless effectless Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 5 NO2 HOCH2CH CHOH NHCOCHCl2 氯霉素 Ph C Ph COCH2CH3 CH2CHN(CH3)2 CH3 Methadone 美散痛 * * * Chloromycetin (+)-Chloromycentin effectless (+)-Methadone effectless