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）Chapter 16 Aldehydes and Ketones I：NucleophilicAddition to the Carbonyl Group（16.9-16.15）The Addition of Hydrogen Cyanide

ORGANIC CHEMISTRY Chapter 16 16.9 The Addition of Hydrogen Cyanide Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 16 16.9 The Addition of Hydrogen Cyanide

ORGANIC CHEMISTRY Chapter 16 OH R OH C=o +HCN S CH CH 3 cN Cyanohydrin (H) (H) -羟基腈 R、OHH2O R、OH-H2O R CHo=C-COH CH 3 CN H or Oh CH3 CO,H a-Hydroxy acid a, B-Unsaturated acid α-羟基酸 ,-不饱和酸 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 16 R C CH3 O + HCN R C CH3 OH CN α−羟基腈 OH (H) (H) Cyanohydrin H+ or OH − R C CH3 OH CO2H R CH2 C CO2H H2O α−羟基酸 α,β−不饱和酸 H2O α−Hydroxy acid α,β−Unsaturated acid R C CH3 OH CN

ORGANIC CHEMISTRY Chapter 16 16.10 The Addition of ylides The Witti g Reaction Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 16 16.10 The Addition of Ylides: The Wittig Reaction

ORGANIC CHEMISTRY Chapter 16 CH2 +CH2=P(C6H5)3 Phosphorus ylide 叶立德 Wittig reaction BuL CH3I +(C6H5)3P-CH3-P(C6H5)3 + CH2-P(C6H4 CH2-P(C6H5)3 Phosphorus ylide叶立德( Wittig reagent) Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 16 CH2 P(C6H5) + 3 O CH2 Phosphorus ylide 叶立德 Wittig reaction CH3I + (C6H5)3P CH3 P(C6H5)3 CH2 P(C6H5)3 CH2 P(C6H5)3 (Wittig reagent) BuLi Phosphorus ylide 叶立德

ORGANIC CHEMISTRY Chapter 16 Mechanism O P(C6H5)3 THE C/+ R2C-P(C6H5) C—C R R AP(C6H5)3 R R C=C、+O=P(C6H5) R R Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 16 Mechanism Mechanism C + O R2C P(C6H5)3 C O C R R P(C6H5)3 C O C R R P(C6H5)3 C C R R + P(C6H5) O 3 THF