ORGANIC CHEMISTRY Chapter 5 5.14 Relating Configurations Through Reactions in Which No Bonds to the stereocenter are Broken 通过未涉及立体中心断键反应相对应的构型 Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 5 5.14 Relating Configurations Through Reactions in Which No Bonds to the Stereocenter are Broken 通过未涉及立体中心断键反应相对应的构型
ORGANIC CHEMISTRY Chapter 5 CH3 CH H-1CH2-OH +H-Cl △ H--CH2-CI+H-OH HOcH CHCH (S)-2-Methy l-1-butano (S)-1-Chloro-2-methylbutane laid 5.756 b=+1.64 CHb-Br CHo-H Zn /h(ZnBr2) H OH H OH retention od configuration CH,CH CHCH (R)-1-Bromo-2-butanol (S)-2-Butanol Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 5 CH3 H CH2 CH2CH3 OH + H Cl ∆ CH3 H CH2 CH2CH3 Cl + H OH (S)-2-Methyl-1-butanol (S)-1-Chloro-2-methylbutane [α]D25 = −5.756 [α]D25 = +1.64 CH2 H OH CH2CH3 Br CH2 H OH CH2CH3 H Zn / H+ (−ZnBr2) retention od configuration (R)-1-Bromo-2-butanol (S)-2-Butanol
ORGANIC CHEMISTRY Chapter 5 5.14 Relative and Absolute Configurations 相对构型与绝对构型 Before 1951 only relative configurations of chiral molecules were known g Configurations of chiral molecules were related to each other through reactions of known stereochemistry o The standard compound was glyceraldehyde CHO CHO H-OH HO-H ChOH Glyceraldehyde CHOH D-(+)-Glyceraldehyde L-()-Glyceraldehyde D-(+)-甘油醛 L()-甘油醛 Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 5 5.14A Relative and Absolute Configurations 相对构型与绝对构型 Before 1951 only relative configurations of chiral molecules were known. Configurations of chiral molecules were related to each other through reactions of known stereochemistry. The standard compound was glyceraldehyde. CHO H OH CH2OH CHO HO H Glyceraldehyde CH2OH D-(+)-Glyceraldehyde D-(+)-甘油醛 L-(–)-Glyceraldehyde L-(–)-甘油醛
ORGANIC CHEMISTRY Chapter 5 CHO COoH CO,H Hgo H OH H OH— H OH [O] CHoO CH,OH CH D-(+)-Glyceraldehyde D-()-Glyceric acid D-()-Lactic acid D-(+)-甘油醛 D-(-)-甘油酸 D-(-)-乳酸 H CHOH的久 CHO CH OH OH H OH CH,OH O] CO,H D-form D-form D-form Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 5 CHO H OH CH2OH D-(+)-甘油醛 CO2H H OH CH2OH D-(−)-甘油酸 CO2H H OH CH3 D-(−)-乳酸 HgO [O] [H] D-(+)-Glyceraldehyde D-(−)-Glyceric acid D-(−)-Lactic acid CHO H OH CH2OH CH3 H OH CH2OH CH3 H OH CO2H D-form D-form D-form [H] [O] ???
ORGANIC CHEMISTRY Chapter 5 o The spatial arrangement of substituents at a chirality center is its absolute configuration o In 1951 Bijvoet using a special technique of X-ray diffraction was able to show conclusively that(+)- tartaric acid had the absolute configuration show below COH H-OH Ho-H CO2 QH L-fo (+)-Tartaric acid Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 5 The spatial arrangement of substituents at a chirality center is its absolute configuration. In 1951 Bijvoet using a special technique of X-ray diffraction was able to show conclusively that (+)- tartaric acid had the absolute configuration show below. CO2H H OH HO H CO2H (+)-Tartaric acid L-form