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第十章 卤 代 烃 ( 8 学时). 10.1 卤代烃的分类和命名法 10.2 卤代烃的制法 10.3 卤代烃的物理性质 10.4 卤代烷的化学性质 10.5 亲核取代和消除的反应机理 10.6 卤代烯烃和卤代芳烃 10.7 重要的卤代烃. 本章教学要求. 掌握卤代烃的分类和命名法; 掌握卤代烃的制法; 了解卤代烃的物理性质; 掌握卤代烷的化学性质; 掌握亲核取代和消除反应机理; 掌握卤代烯烃和卤代芳烃的结构特点和性质; 了解一些重要的卤代烃的性质和用途。. 卤代烃的概念. - PowerPoint PPT Presentation
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810.1 10.2 10.3 10.4 10.5 10.6 10.7
C-BrC-Cl
10.110.1.1 1.
10.110.1.1 2CH3CH2Br RXClCH2CH2Cl CH3CHBr2
10.110.1.1 3(CH3)2CHCH2Cl()CH3CH2CHBrCH3()(CH3)3C-I()
10.110.1.2 1.:
10.110.1.2 2. :(1) ,(2) (3)
10.1
10.1
10.13.:,,10.1.2
10.1 4. (1), 1--2-10.1.2
10.1 4. (2),, 3131210.1.2
10.1
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-
P144----14,4--3--1-(7) BrCH2CH2CHClC(CH3)33--5-3,5-
P144----2 (1) 1--3-(2) 1--4--1-(3) 1--1-(4)1--2-
10.210.2.1 1. ,,
10.210.2.12. -, -
10.210.2.13. ,
10.210.2.13. ,
10.210.2.2 ,
10.2 ,10.2.2
10.210.2.3 ,(),
-Ar-CH2-Cl- Ar-CH2-OH Ar-CH2-OR Ar-CH2-CN Ar-CH2-NH2
10.210.2.4 (HX) (PX3)(SOCl2)+ZnCl2
10.210.2.4
P146----31-2HCl-
10.310.3.1 ,,: ,
,,,
10.310.3.1 3. CRI > RBr > RCl4.XCH3ClCH2Cl2CCl4
P---- 19
P---- 1
1.2.3.4.
10.4 CX CX ()
10.4CX CFCH CF 439 CH CCl CBr CI KJ/mol 414 339 285 218
CX CH
, C=C C-IC-BrC-Cl 10.4
10.4
10.410.4.1--
10.41.10.4.1
10.41. 1NaOH210.4.1
10.4. RONa10.4.1
10.4. R-X1RX,R-O-R--10.4.1
10.4. 10.4.1 qng NCCN 1. 2.(CN) 2 ,() HCN,KCN,NaCN jng RCN(,),, -
10.4. 10.4.1
10.4. COOH[CONH2] 10.4.1
10.4. 10.4.1
10.4.10.4.1
10.4.10.4.1
10.410.4.1
10.4 5.AgNO3 10.4.1
10.45.AgNO3: (CH2=CH-CH2X) RIRBr RCl10.4.1
10.4. 10.4.1
10.4.10.4.1
10.410.4.2
10.410.4.2
10.410.4.2I()
10.4.210.4
10.4.210.4
(Saytzeff rule) CH 10.4
(Saytzeff rule)10.4
(Saytzeff rule)10.4
10.4
P151----7CH3-CH=CH-CH=CH-CH3
10.4.3
(M=NaK) (M=MgLi) (M=Pb,SnHg)10.4
RMgX 10.410.4.3
THF10.410.4.3
RMgX10.410.4.3
10.410.4.3
10.410.4.3
10.410.4.3
19124110.410.4.3
P153----8
P--0
--
10.5 CXCX
SNSN(Substitutional[sbstitju:nl]Nucleophilic[nju:kliufilik]10.5
10.5LLeaving group
H2O , NH3 , OH-, RO-, CN- 10.510.5.1
10.5.1 ,SN -- SN2 -- SN110.5
1.SN2 80%-20%, (NaOHKOH)SN2 + CH3-Br HO-CH3 +
,SN2 10.5.1Br-10.5
SN2: 10.5C-BrC-OC-Osp3sp3sp2
SN2:
SN2SP3SP2SP310.5
CH3BrCH3BrOH - SN2 SN210.5
SN2:1 Nu-L10.5
2 Walden SN2:10.5RS
CH3BrOH SN2
SN2
SN2,sp3sp2sp2sp3SN2
SN2OHCBrwaldenSN2
SN2
2.SN110.5
SN1
2.SN1:10.5
SN12.SN110.5
SN1 10.5
2.SN1 SN1,(CH3)3C-BrBr-,HO-,,,10.5
2.SN1 SN110.5
SN1 1 + SN1sp2 10.5
2 > SN1 > SN110.5
SN1 SN1
T1T2sp2OH 50%)SN110.5
3.SN SN1SN210.5
3.SN (1)10.5
3.SN SN1SN2(1)10.5SN2SN1
3.SN SN1SN2
(1)10.5SN1SN2
SN2 r (2)(CH3)3C-Br : 3.SN (1)10.5
SN2 SN2- C,SN2 SN2
3.SN (1)10.5
SN2 3.SN 1.5105 - C- C(1)10.5
3.SN (1) SN1 SN1SN1 SN1
10.5
3.SN SN1SN1108(1) SN110.5
SNSN13RX > 2RX > 1RX > CH3XSN2CH3X > 1RX > 2RX > 3RX
SN1SN2
(2) SN1SN2,C-X(X),, SN1SN2 3.SN 10.5
(2) I-,Br-,Cl-,,;HO-,RO-,,,, RI>RBr>RCl 3.SN 10.5
(2) SN1SN2 RO-HO-R-OHRORH+ ROH2+ Br-+ROH RBr+HO- ROH+ H++ Br- RBr+H2O 3.SN 10.5
P18----1011 1213
SN2SN1
10.5.2 (E1)(E2).10.5
E2HO- E2 eliminate[ilimineit] 10.5.2 1.(E2)10.5
10.5.21.(E2)E210.5
10.5.2 1.(E2)R-CH2-CH2-X+OH -R-CH2-CH2-OH +X - OHOHOHE2 OHSN210.5
10.5.22.(E1) 10.5
10.5.22.(E1) 10.5
10.5.22.(E1) (CH3)3C-OH E1SN1-E1SN110.5
10.5.2 10.5
SN1E1( SN2E23RX1RX!!!CHCHCXCX
P160----14
E1
10.6Xsp2Cl
p- p- 10.6.110.6
10.6
lCH2=CH-Cl,10.6
10.6.2 p- 10.6
AgNO3-
10.6.3 P16110.6
P----,
10.7.1 61.2,10.7.2 76.5
10.7
P- 1 6