3. Hydrogenation of C=o, c=N and c=N bonds ——醇、醛、胺的制备 O O CH3CH,CCI H2 CHrCh,CH CH2CHoChOH Pd/c an acyl chloride an aldehyde a primary alcohol ■酰卤的催化氢化在部分钝化的催化剂作用下 可以停留在醛的阶段— Rosenmund还原 0 CH3 CH,CCI CH3 CH,CH partially an acyl chloride deactivated an aldehyde Pd
3. Hydrogenation of C=O, C=N and C 3. Hydrogenation of C=O, C=N and C ≡N bonds N bonds ——醇、醛、胺的制备 醇、醛、胺的制备 酰卤的催化氢化在部分钝化的催化剂作用下 可以停留在 醛的阶段——Rosenmund还原
二、还原反应一催化氢化 3. Hydrogenation of C=o, c=n and c=n bonds H CH3CH,COh 2 no reaction a carboxylic acid Raney O Ch ChoCOCH →> no reaction Raney ni an ester O 2 CH3 CH,CNHCH3 Raney no reaction Ni an amide 羧酸、酯和酰胺在特殊的催化剂和苛刻的条件氢化可以还原
二、还原反应 — 催化氢化 3. Hydrogenation of C=O, C=N and C 3. Hydrogenation of C=O, C=N and C ≡N bonds N bonds 羧酸、酯和酰胺在特殊的催化剂和苛刻的条件氢化可以还原
4.其它基团的还原 ①苄基醚(或硫醚)的还原(去保护) CH2-sCH2Ph CH H,, Raney ni 3 OCHPh OH ②硝基化合物的还原(芳香胺的合成) CH CH 3 3 NO 人NH H2, Raney ni CH(CH3)2 CH(CH3)
4. 其它基团的还原 ① 苄基醚（或硫醚）的还原（去保护） 苄基醚（或硫醚）的还原（去保护） CH2-SCH2Ph OCH2Ph H2 , Raney Ni CH3 OH ② 硝基化合物的还原（芳香胺的合成） 硝基化合物的还原（芳香胺的合成） CH3 CH(CH3)2 NO2 H2 , Raney Ni CH3 CH(CH3)2 NH2
二、还原反应一催化氢化 5. Relative reactivity of the Functional Groups by catalytic Hydrogenation TABLE 18.1 Relative Ease of Reduction of Functional Groups by Catalytic Hydrogenation RCC1>RC≡CR>RCH>RCH=CHR>RCR>RC≡N>RCH=NR yl chloride alkyne aldehyde alkene ketone nitrile Imine increasing reactivity toward H2, Pd/c Cannot be reduced by catalytic hydrogenation RCOR RCNHR RCOH ester amide carboxylic acid
二、还原反应 — 催化氢化 5. Relative reactivity of the Functional Groups by Catalytic Hydrogenation
1mol h Ph-HC=CH-C-Ph Pd/CPh-H2C—CH2CPh Ph-HC-CH-CHmol I Pd/c Ph-HC=CH-CH 2OH Ph-HC=CH-CH PhH2c—cH2CH HC1△ Imol h Ph-HC=CH-CH Pd/c Ph-H,,-CH
Ph-HC CH-CH O 1mol H2 Pd / C Ph-HC CH-C-Ph O 1mol H2 Pd / C Ph-HC CH-CH2OH Ph-H2C CH2-C-Ph O Ph-H2C CH2-CH O Ph-HC CH-CH O ? Ph-HC CH-CH O O 1mol H2 Pd / C Ph-H2C CH2-CH O O HCl