西北农林科技大学：《有机化学 Organic chemistry》课程教学课件（2012）Chapter 06 Stereochemistry

Organic Chemistry,6th Edition L.G.Wade,Jr Chapter 6 Stereochemistry 王俊儒应用化学系17室87092187(0)

Chapter 6 Stereochemistry Organic Chemistry, 6th Edition L. G. Wade, Jr. 王俊儒 应用化学系417室 87092187(O)

Content Molecular Chirality Chiral carbon Absolute and Relative Configuration Stereoisomers without chiral carbons Properties of Enantiomers Diastereomers Resolution of Enantiomers

Content Molecular Chirality & Chiral carbon Absolute and Relative Configuration Stereoisomers without chiral carbons Properties of Enantiomers & Diastereomers Resolution of Enantiomers

Key Notes Stereochemistry Chiral enantiomers Chirality Chiral center Optical rotations R/S,D/L Diastereomers meso forms Resolution of enantiomers

Key Notes Stereochemistry Chiral enantiomers Chirality & Chiral center Optical rotations R /S ，D/L Diastereomers meso forms Resolution of enantiomers

Sec 1 Chirality Handedness":right glove doesn't fit the left hand. Mirror-image object is different from the original object. right hand left hand Copyright 2005 Pearson Prentice Hall,Inc

Sec 1 Chirality  “Handedness ”: right glove doesn ’t fit the left hand. Mirror-image object is different from the original object

Chirality right hand left hand right hand left hand plus mitten ◆ plus mittne plus left glove plus right glove ■ left hand left hand right hand right hand plus right glove plus left glove plus mug ◆ plus mug

Chirality

Chirality A molecule is chiral if its two mirror image forms are not superposable upon one another. A molecule is achiral if its two mirror image forms are superposable

Chirality A molecule is chiral if its two mirror image forms are not superposable upon one another. A molecule is achiral if its two mirror image forms are superposable

Bromochlorofluoromethane is chiral It cannot be superposed point for point on its mirror image. B Br 7 111111T To show nonsuperposability,rotate this model 180 around a vertical axis

Br Cl H F Bromochlorofluoromethane Bromochlorofluoromethane is chiral H Cl Br F To show nonsuperposability, rotate this model 180° around a vertical axis. It cannot be superposed point for point on its mirror image

Bromochlorofluoromethane is chiral Br 1111111111111111111

Br Cl H F Bromochlorofluoromethane Bromochlorofluoromethane is chiral H Cl Br F

Another look 1111111711111

Another look Another look

Enantiomers nonsuperposable mirror images are called enantiomers and are enantiomers with respect to each other

are enantiomers with respect to each other and nonsuperposable mirror images are called enantiomers Enantiomers Enantiomers