第十章 卤 代 烃 （ 8 学时）

810.1 10.2 10.3 10.4 10.5 10.6 10.7

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C-BrC-Cl

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10.110.1.1 1.

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10.110.1.1 2CH3CH2Br RXClCH2CH2Cl CH3CHBr2

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10.110.1.1 3(CH3)2CHCH2Cl()CH3CH2CHBrCH3()(CH3)3C-I()

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10.110.1.2 1.:

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10.110.1.2 2. :(1) ,(2) (3)

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10.1

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10.1

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10.13.:,,10.1.2

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10.1 4. (1), 1--2-10.1.2

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10.1 4. (2),, 3131210.1.2

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10.1

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P144----1(1) (CH3)3CCH2Br2,2--1-(2) CH3CCl2CH2CH2CH32,2-(3)CH3(CH2)3CHBrCHClCHF21,1--2--3-(4) CH3CH2C(CH3)2Cl2--2-1--1,3-

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P144----14,4--3--1-(7) BrCH2CH2CHClC(CH3)33--5-3,5-

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P144----2 (1) 1--3-(2) 1--4--1-(3) 1--1-(4)1--2-

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10.210.2.1 1. ,,

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10.210.2.12. -, -

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10.210.2.13. ,

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10.210.2.13. ,

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10.210.2.2 ,

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10.2 ,10.2.2

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10.210.2.3 ,(),

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-Ar-CH2-Cl- Ar-CH2-OH Ar-CH2-OR Ar-CH2-CN Ar-CH2-NH2

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10.210.2.4 (HX) (PX3)(SOCl2)+ZnCl2

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10.210.2.4

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P146----31-2HCl-

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10.310.3.1 ,,: ,

,,,

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10.310.3.1 3. CRI > RBr > RCl4.XCH3ClCH2Cl2CCl4

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P---- 19

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P---- 1

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1.2.3.4.

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10.4 CX CX ()

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10.4CX CFCH CF 439 CH CCl CBr CI KJ/mol 414 339 285 218

CX CH

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, C=C C-IC-BrC-Cl 10.4

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10.4

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10.410.4.1--

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10.41.10.4.1

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10.41. 1NaOH210.4.1

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10.4. RONa10.4.1

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10.4. R-X1RX,R-O-R--10.4.1

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10.4. 10.4.1 qng NCCN 1. 2.(CN) 2 ,() HCN,KCN,NaCN jng RCN(,),, -

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10.4. 10.4.1

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10.4. COOH[CONH2] 10.4.1

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10.4. 10.4.1

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10.4.10.4.1

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10.4.10.4.1

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10.410.4.1

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10.4 5.AgNO3 10.4.1

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10.45.AgNO3: (CH2=CH-CH2X) RIRBr RCl10.4.1

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10.4. 10.4.1

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10.4.10.4.1

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10.410.4.2

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10.410.4.2

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10.410.4.2I()

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10.4.210.4

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10.4.210.4

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(Saytzeff rule) CH 10.4

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(Saytzeff rule)10.4

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(Saytzeff rule)10.4

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10.4

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P151----7CH3-CH=CH-CH=CH-CH3

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10.4.3

(M=NaK) (M=MgLi) (M=Pb,SnHg)10.4

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RMgX 10.410.4.3

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THF10.410.4.3

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RMgX10.410.4.3

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10.410.4.3

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10.410.4.3

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10.410.4.3

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19124110.410.4.3

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P153----8

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P--0

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--

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10.5 CXCX

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SNSN(Substitutional[sbstitju:nl]Nucleophilic[nju:kliufilik]10.5

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10.5LLeaving group

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H2O , NH3 , OH-, RO-, CN- 10.510.5.1

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10.5.1 ,SN -- SN2 -- SN110.5

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1.SN2 80%-20%, (NaOHKOH)SN2 + CH3-Br HO-CH3 +

,SN2 10.5.1Br-10.5

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SN2: 10.5C-BrC-OC-Osp3sp3sp2

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SN2:

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SN2SP3SP2SP310.5

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CH3BrCH3BrOH - SN2 SN210.5

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SN2:1 Nu-L10.5

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2 Walden SN2:10.5RS

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CH3BrOH SN2

SN2

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SN2,sp3sp2sp2sp3SN2

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SN2OHCBrwaldenSN2

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SN2

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2.SN110.5

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SN1

2.SN1:10.5

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SN12.SN110.5

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SN1 10.5

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2.SN1 SN1,(CH3)3C-BrBr-,HO-,,,10.5

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2.SN1 SN110.5

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SN1 1 + SN1sp2 10.5

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2 > SN1 > SN110.5

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SN1 SN1

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T1T2sp2OH 50%)SN110.5

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3.SN SN1SN210.5

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3.SN (1)10.5

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3.SN SN1SN2(1)10.5SN2SN1

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3.SN SN1SN2

(1)10.5SN1SN2

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SN2 r (2)(CH3)3C-Br : 3.SN (1)10.5

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SN2 SN2- C,SN2 SN2

3.SN (1)10.5

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SN2 3.SN 1.5105 - C- C(1)10.5

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3.SN (1) SN1 SN1SN1 SN1

10.5

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3.SN SN1SN1108(1) SN110.5

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SNSN13RX > 2RX > 1RX > CH3XSN2CH3X > 1RX > 2RX > 3RX

SN1SN2

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(2) SN1SN2,C-X(X),, SN1SN2 3.SN 10.5

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(2) I-,Br-,Cl-,,;HO-,RO-,,,, RI>RBr>RCl 3.SN 10.5

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(2) SN1SN2 RO-HO-R-OHRORH+ ROH2+ Br-+ROH RBr+HO- ROH+ H++ Br- RBr+H2O 3.SN 10.5

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P18----1011 1213

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SN2SN1

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10.5.2 (E1)(E2).10.5

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E2HO- E2 eliminate[ilimineit] 10.5.2 1.(E2)10.5

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10.5.21.(E2)E210.5

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10.5.2 1.(E2)R-CH2-CH2-X+OH -R-CH2-CH2-OH +X - OHOHOHE2 OHSN210.5

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10.5.22.(E1) 10.5

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10.5.22.(E1) 10.5

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10.5.22.(E1) (CH3)3C-OH E1SN1-E1SN110.5

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10.5.2 10.5

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SN1E1( SN2E23RX1RX!!!CHCHCXCX

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P160----14

E1

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10.6Xsp2Cl

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p- p- 10.6.110.6

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10.6

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lCH2=CH-Cl,10.6

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10.6.2 p- 10.6

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AgNO3-

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10.6.3 P16110.6

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P----,

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10.7.1 61.2,10.7.2 76.5

10.7

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P- 1 6

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