上海交通大学：《有机化学》教程教学资源（英文讲稿）06 Stereochemistry

p35 6. Stereochemistry

6. Stereochemistry p.35

R、RRR RRR R R R R R" CHen (CH2)n R R R

R'' R''' R R' R'' R' R R''' (CH2 )n R R' R'' R''' (CH2 )n R R' R'' R

H H H H R

H HH H H H H H H H H R H R H

objects are not the same as their mirror images -The property is commonly called handedness手性) handedness results from substitution patterns on sp3 hybridized carbon

• objects are not the same as their mirror images –The property is commonly called “handedness(手性)” • handedness results from substitution patterns on sp3 hybridized carbon

CHeX H、H H CHOY H\Y CHXYZ Left hand Right hand H、Y 92004 Thomson/Brooks Cole

p38 The reason for handedness in molecules: chirality 分子中的手性由何而来 bed

The reason for handedness in molecules: chirality 分子中的手性由何而来 Cabcd p.38 m C C a b c b a c d d

(R}桔味(S}-柠檬味

H H (R)-桔味 (S)-柠檬味 苧烷

HH ON C—C—CH2OH OH NH2 氯霉素 HH ON C-C-CH2OH OH NH2

氯霉素 O2N C C CH2OH OH NH2 H H O2N C C CH2OH OH NH2 H H

OH OH OCH2-C-CH2NHPr OCH -C-CHoNHPr H H (R-避孕药 (S)-心得宁

(R)-避孕药 (S)-心得宁 OCH2 C CH2NHPr H OH OCH2 C CH2NHPr H OH

Thalidomide (R) O (S)-

N N O O O O H Thalidomide (R)- N N O O O O H (S)-