上海交通大学：《有机化学》教程教学资源（英文讲稿）07 Alkyl halides

p221 7. Alkyl halides Ⅹδ 0+

7. Alkyl Halides p.221 X C d + d -

What Is an alkyl halide An organic compound containing at least one carbon-halogen bond (C) X(F, Cl, Br, D replaces h Can contain many c-X bonds

What Is an Alkyl Halide • An organic compound containing at least one carbon-halogen bond (C-X) –X (F, Cl, Br, I) replaces H • Can contain many C-X bonds

β六六六 六六六 BI-NN-BI O 二溴海因

Cl Cl Cl Cl ClCl Cl Cl Cl Cl Cl Cl b-六六六 g-六六六 N N O O Br Br 二溴海因

C l CH CH Cl DDT 1874~1900~1972 1939 Miller P, (1948 Nobel Prize) LD≥:250 CC CHO CH OCH DMDDT LD0:6000 LD3mng/Kg50%死亡率的剂量

DDT Cl CH Cl CCl3 Cl CH Cl CH2 1874~1900~1972 1939 Miller P.,(1948 Nobel Prize) LD50:250 CH3O CH OCH3 CCl3 DMDDT LD50:6000 LD50(mg / Kg): 50%死亡率的剂量

OH OCHoCOH Naoh CICH Na CHOH then ho CI aa 24.5-T oXIn Seveso, Italy ( 1976)

Cl Cl Cl OH Cl Cl Cl Cl NaOH CH3OH ClCH2CO2Na then HCl Cl Cl Cl OCH2CO2H O O Cl Cl Cl Cl dioxin 2,4,5-T Seveso, Italy(1976)

LDk: 2lppm O H ROH CH2-N=C-O RO-C-N-CH3 MIC O H 0-C-N-CH3 Pradash Ind(1984) HoO CH3-N==0-CHBNH2tco2 4H=-100KJ CH 3CH3-N=C=O AH=-200KJ CH CH

CH3 N C O O C N O H CH3 MIC H2O CO2 ROH CH3NH2 RO C N H CH3 O CH3 N C O + 3 CH3 N C O N N N O O O CH3 CH3 CH3 LD50:21ppm DH = - 100KJ DH = - 200KJ Pradash, India(1984)

甏冼殛煤油(1845;四氯化碳 (1897);三(四)氯乙烯(930-) 织物保护氟碳化物 (Scotchgard, 3M) 血袋PVC 轮脍CD:话脑 ●●●● RX可阻有机汞的生成

乾洗剂: 煤油(1845); 四氯化碳 (1897); 三(四)氯乙烯(1930~) 织物保护剂: 氟碳化物 (Scotchgard, 3M) 血袋: PVC 轮胎; CD; 电话(脑)······ RX可阻止有机汞的生成

natural products Brr O C I 0 Tetrachloromertensene H 3E Laureatin CH3 Br C HO OCH Br 1998 Gribble.w.acc. 1998.31.141

natural products: Tetrachloromertensene 3 E - Laureatin Cl Cl Cl Br Br O Br O H Cl Cl Cl Cl CH3 HO OCH3 Cl Cl Cl 1998 Gribble G.W. Acc. 1998, 31, 141

NH CO thyroxine(甲状腺素) Kendall. c,1915(分离 Harington CR,1927(结构、合 成)

Thyroxine(甲状腺素) Kendall E.C., 1915(分离) Harington C.R., 1927(结构、合 成） O NH3 + CO2 - I I I I(H) HO

7. 1 Naming Alkyl Halides Name is based on longest carbon chain Contains double or triple bond if present Number from end nearest any substituent(alkyl or halogen) CHs Br Br CH Ch. CHCHOCHCHCHoCH CH3CHCH2CHCHCH2CH3 23456-7 123145 CH CH B- Bromo: 2 4-dimethvlhentane 2-Bromo-4.5-dimethvIheptane

7.1 Naming Alkyl Halides • Name is based on longest carbon chain – (Contains double or triple bond if present) –Number from end nearest any substituent (alkyl or halogen)