卤代烃CH,CH,CICH,CH,BrCH,CH,I偶极矩2.05D2.03D1.91D极化度（极化率）：共价键对外界电场的感受能力不同卤代烃的静态极性次序(CH3)3C-X > (CH3)2CH-X > CH3CH2-X > CH3-X
卤代烃 CH3CH2Cl CH3CH2Br CH3CH2 I 偶极矩 2.05D 2.03D 1.91D 极化度（极化率）：共价键对外界电场的感 受能力 不同卤代烃的静态极性次序 (CH3) 3 C-X > (CH3) 2 CH-X > CH3 CH2-X > CH3-X
9.2.3.1 Nucleophilic SubstitutionCCX + Nu:NuR-R-C+产物底物亲核试剂离去基团亲核取代反应：由富电子试剂进攻缺电子中心而进行的取代反应
9.2.3.1 Nucleophilic Substitution 亲核取代反应：由富电子试剂进攻缺电子中心而进行的 取代反应 底物 亲核试剂 产物 离去基团 + - R C X + Nu: - R C Nu + X -
(1) HydrolysisRX +OH> R-OH +(2)Alcoholysisor phenolysisRONa → ROR+ NaXRX +ArONa → ArOR + NaX
(1) Hydrolysis (2) Alcoholysis or phenolysis ▽ R X + OH R OH + X RX + RONa 1 R1 OR + NaX ArONa ArOR + NaX
(3)AmmonolysisNH3RNH2 + HXRX +H2NR1 —RNHR1 + HXCH3CH3CH3CH3CH30CH2C0CINH2 + Br-CHCO0CH3NHCHCOOCH3CH3CH3CH3CH3CHCOOCH3甲霜灵（杀菌剂）COCH,OCH3CH3
(3) Ammonolysis NH3 RNH2 + HX H2 NR1 RNHR1 + HX RX + CH3 CH3 NH2 + Br CHCOOCH3 CH3 CH3 CH3 NHCHCOOCH3 CH3 CH3OCH2COCl CH3 CH3 N CHCOOCH3 CH3 COCH2OCH3 甲霜灵(杀菌剂)
(4)Reactionwithmetal cyanide乙醇R-X + NaCNR-CN+ NaX腈H20RCOOHH orOH
(4) Reaction with metal cyanide 乙醇 R X + NaCN ▽ R CN+ NaX RCOOH 腈 H2 O H orOH