【正文】 d i h a l i d e s C CX XC C + Z n X 2Z nE x a m p l e s :C H 3 C H B r C H B r C H 32 , 3 D i b r o m o b u t a n eC H 3 H C C H C H 32 B u t e n eZ n4 . R e d u c t i o n o f a l k y n e sR C C RH 2L i n d l a r c a t a l y s tN a o r L i , N H 3C CR RH HS y nC CRHHRA n t iPreparation of Alcohol 1. OxymercurationDemercuration 2. HydroborationOxidation 3. Grignard Synthesis 4. Hydrolysis of Alkyl Halides 5. Hydroxylation of Alkenes Preparation of Alcohol 1 . O x y m e r c u r a t i o n d e m e r c u r a t a i o nC CH g ( O A c ) 2H 2 OC CO H H g O A cN a B H 4C CO H HM e r c u r i c a c e t a t eM a r k o v n i k o va d d i t i o n2 . H y d r o b o r a t i o n O x i d a t i o nC C C CH BC CH O HA n t i M a r k o v n i k o va d d i t i o n( B H 3 ) 2D i b o r a n eH 2 O 2 , O H 3 . G r i g n a r d s y n t h e s i sC O R M g X+ CRO M g X CRO HH 2 O4 . H y d r o l y s i s o f a l k y l h a l i d e sR X + O H ( o r H 2 O ) R O H + X ( o r H X )E x a m p l e s :C H 2 C lN a O HH 2 OC H 2 O HB e n z y l c h l o r i d e B e n z y l a l c o h o lCC H 3H 3 CC H 3C lH 2 O / H+CC H 3H 3 CC H 3O H5 . H y d r o x y l a t i o n o f a l k e n e sC CK M n O4o r H I O4R C O2O HC CO H O HOC CH 2 O , H+C CO HO Hs y n H y d r o x y l a t i o na n t i H y d r o x y l a t i o n6 . A l d o l c o n d e n s a t i o n7 . R e d u c t i o n o f c a r b o n y l c o m p o u n d s8 . R e d u c t i o n o f a c i d a n d e s t e r sPreparation of Halide 1. From Alcohols 2. Halogenation of Certain hydrocarbons 3. Addition of Hydrogen Halide to Alkenes 4. Addition of Halogen to Alkenes and Alkynes 5. Halide Exchange Preparation of Halide 1 . F r o m a l c o h o l sR O H R XH X o r P X 3E x a m p l e s :C H 3 C H 2 C H 2 O Hc o n . H B r o rN a B r , H 2 S O 4 h e a tC H 3 C H 2 C H 2 B rn P r o p y l a l c o h o l n P r o p y l b r o m i d eC H C H 3O HP B r 3C H C H 3B r1 P h e n y l e t h a n o l 1 B r o m o 1 p h e n y l e t h a n eC H 3 C H 2 O H P , I 2 C H 3 C H 2 IE t h y l a l c o h o l E t h y l i o d i d e2 . H a l o g e n a t i o n o f c e r t a i n h y d r o c a r b o n sR H R XX 2E x a m p l e s :C H 3B r 2h vC H 2 B rT o l u e n e B e n z y l b r o m i d eCC H 3C H 3C H 3C H 3C l 2h vCC H 3C H 3C H 3C H 2 C lN e o p e n t a n e N e o p e n t y l c h l o r i d e3 . A d d i t i o n o f h y d r o g e n h a l i d e t o a l k e n e sC C C CH XH X4 . A d d i t i o n o f h a l o g e n t o a l k e n e s a n d a l k y n e sC C C CX XX 2C C C CX XX XX 25 . H a l i d e e x c h a n g eR X I R Ia c e t o n e+Preparation of Ether 1. Williamson Synthesis 2. AlkoxymercurationDemercuration Preparation of Ether 1 . W i l l i a m s o n s y n t h e s i sR X +R 39。o rR O A rY i e l d f r o m R X :C H 3 1 o 2 o ( 3 o )E x a m p l e s :( C H 3 ) 2 C H O N a + + C H 3 C H 2 C H 2 B r C H 3 C H 2 C H 2 O C H 2 ( C H 2 ) 2 C H 3S o d i u mi s o p r o p o x i d en P r o p y lb r o m i d e I s o p r o p y l n p r o p y l e t h e rO H + C H 3 C H 2 B ra q . N a O HO C H 2 C H 3P h e n o l E t h y l b r o m i d e E t h y l p h e n y l e t h e r2 . A l k o x y m e r c u r a t i o n d e m e r c u r a t i o nC C + R O H C CR O H g O 2 C C F 3H g ( O 2 C C F 3 ) 2 C CR O H+N a B H 4A l k e n e M e r c u r i ct r i f l u o r o a c e t a t e M a r k o v n i k o vo r i e n t a t i o nPreparation of Alkylbenzene 1. FriedelCrafts Alkylation 2. Conversion of Side Chain Preparation of Alkylbenzene 1 . F r i e d e l C r a f t s a l k y l a t i o n+ R XL e w i s a c i dR + H X R m a y r e a r r a n g eL e w i s a c i d : A l C l 3 , B F 3 , H F , e t c .A r X c a n n o t b e u s e d i n p l a c e o f R XC H 3 C H C H 2 C H 3C lC H 3 C H 2 C H 2 C H 2 C lE x a m p l e s :++A l C l 3CC H 3C H 2 C H 3C H 2 C H 2 C H 2 C H 3c h i e f p r o d u c t2 . C o n v e r s i o n o f s i d e c h a i nROZ n ( H g ) n , H C lo r N2H4, b a s eC H 2 RC l e m m e n s e n o r W o l f f K i s h n e r r e a c t o i nC H C H R C H 2 C H 2 RH2 / C a tPreparation of Phenol 1. Hydrolysis of Diazonium Salts 2. Alkli Fusion of Sulfonates Preparation of Phenol 1 . H y d r o l y s i s o f d i a z o n i u m s a l t sA r N 2 + H 2 O A r O H + +N 2 H +E x a m p l e :N 2+ H S O 4C l C lO H+ N 2H 2 O , H+, h e a tm C h l o r o b e n z e n e d i a z o n i u m h y d r o g e n s u l f a t em C h l o r o p h e n o l2 . A l k a l i f u s i o n o f s u l f o n a t e sS O 3 N aN a O H , H 2 O3 0 0oCON a+d i l . H 2 S O 4O H S o d i u m2 n a p h t h a l e n e s u l f o n a t e S o d i u m2 n a p h t h o x i d e 2 N a p h t h o lPreparation of Amine 1. Reduction of Nitro Compounds 2. Reaction of Halides with ammonia or Amines 3. Reductive Amination 4. Reduction of Nitriles 5. Hofmann Degradation of Amides Preparation of Amine 1 . R e d u c t i o n o f n i t r o c o m p o u n d sA r N O 2R N O 2o rm e t a l , H +o r H 2 , c a t .A r N H 2R N H 2o r c h i e f l y f o r