有機(jī)合成課件第2章基礎(chǔ)有機(jī)合成-文庫吧資料
2025-01-26 07:06本頁面
【正文】 i d e n t i f i c a i t o nN H 2 N H 2N H 2 N H C 6 H 5N H 2 N H C O N H 2H y d r o x y l a m i n eH y d r a z i n eP h e n y l h y d r a z i n eS e m i c a r b a z i d eO x i m eH y d r a z o n eP h e n y l h y d r a z o n eS e m i c a r b a z o n eC NC N N H 2C N N H C 6 H 5C N N H C O N H 2O HN H 2 O HB e n z a l d e h y d e p h e h y l h y d r a z o n eA c e t a l d o x i m eC NC N N H C 6 H 5O HHH 3 CHC 6 H 55. Addition of alcohols +C O 2 R O H H + C O RO RExample: + H+C O C H 2 C H 3O C H 2 C H 32 C H 3 C H 2 O HC H 3 C OH HC H 36. Cannizzaro reaction +C OH2 s t r o n g b a s e C H 2 O HC O O Examples: +H C OH2 C H 3 O HH C O O 5 0 % N a O H+25 0 % N a O HC H OC lC O O C lC H 2 O HC l+ H C O O 5 0 % N a O HC H OO C H 3C H 2 O HO C H 3O C H 3 O C H 3C H 2 O +7. Addition of Grignard reaction 8. Others R M g XHC O HRHHC O HRR 39。RC r O 3 o r K 2 C r 2 O 7Example: C H 3HO HC HH 3 C C H 3K 2 C r 2 O 7 H 2 S O 4C H 3C HH 3 C C H 3O2. FriedelCrafts acylation +R C O C l R C O A rL e w i s a c i dA r HExamples: +n C 5 H 1 1 C O C l n C 5 H 1 1 C OC a p r o y l c h l o r i d e n p e n t y l p h e n y l k e t o n eA l C l 3+ A l C l 3C O C l C OB e n z o y l c h l o r i d e B e n z o p h e n o n e( D i p h e n y l k e t o n e )Reactions of Aldehyde amp。 Ketone 1. Oxidation of primary alcohols Example: P y r i d i n i u m c h l o r o c h r o m a t eC OHC H 3 C H 2 C H 2C H 3 C H 2 C H 2 C H 2 O Hn B u t y l a l c o h o l1 B u t a n o ln B u t y l a l d e h y d eB u t a n a l2. Oxidation of methylbenzene C l 2 , h e a tC r O 3 / A c 2 OA r C H C l 2A r C H ( O O C C H 3 ) 2A r C H OA r C H 3 H 2 OExamples: H 2 OB rC H 3B rC H C l 2B rC H OC l 2 , h e a t , h vp B r o m o t o l u e n e p B r o m o b e n z a l d e h y d eC r O 3 / A c 2 O H2 ON O 2C H ON O 2C H 3N O 2C H ( O A c ) 2p N i t r o t o l u e n e p N i t r o b e n z a l d e h y d e3. Reduction of acid chloride R C O C l o r A r C O C l L i H ( O B u n ) 3 R C H O o r A r C H OExample: N O 2C O C lL i H ( O B u n ) 3N O 2C H O1. Oxidation of secondary alcohols 2 o a l c o h o l K e t o n eR C H R 39。C H 3 C H 2 C lE t h y l c h l o r i d e E t h y l l i t h i u m L i t h i u md i a l k y l c o p e rC H 3 C H 2C H 3 C H 2C H 3 C H 2C u L i C H 3 ( C H 2 ) 5 C H 2 B rn H e p t y l b r o m i d eC H 3 C H 2 C H 2 ( C H 2 ) 5 C H 3n N o n a n eL iL iC u I Preparation of Alkene 1. Dehydrohalogenation of Alkyl Halide 2. Dehydration of Alcohols 3. Dehalogenationof Vicinal Dihalides 4. Reduction of Alkynes Preparation of Alkene 1. Dehydrohalogenation of alkyl halide CHCXC CK O H K X H 2 Oa l c o h o lE a s e o f d e h y d r o h a l o g e n a y i o no f a l k y l h a l i d e s 3 o 2 o 1 o+ ++Examples: C H 3 C H 2 C H 2 C H 2 C ln B u t y l c h l o r i d e 1 B u t e n eK O H ( a l c o h o l ) C H3 C H 2 H C C H 2K O H ( a l c o h o l )C H3 C H 2 C H C l C H 32 B u t e n e 8 0 % 1 B u t e n e 2 0 %C H 3 C H 2 H C C H 2C H 3 H C C H C H 3s e c B u t y l c h l o r i d e2. Dehydration of alcohols CHCO HC C H 2 O+a c i d E a s e o fd e h y d r o g e n a t i o n o f a l c o h o l s3 o 2 o 1 oExamples: 2 B u t e n eC H 3 H C C H C H 3a c i dC H 3 C H 2 C H 2 C H 2 O Hn B u t y l a l c o h o l 1 B u t e n eC H 3 C H 2 H C C H 2C h i e f p r o d u c ta c i dC h i e f p r o d u c tC H 3 C H 2 C H O H C H 32
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鄂ICP備17016276號-1