《有机化学》课程PPT教学课件（Organic Chemistry, William A. Price, Ph.D. PPT, La Salle University, L.G.WADE, JR., 8th Edition）Chemistry of Aromatic Compounds

Intermediate is Resonance-Stabilized H ⊕ ⊕

Intermediate is Resonance-Stabilized C O R H C O R H C O R H

An Acylation CH3 CH3 CH3CH2CHCH2CCI CCH2CH2CHCH TiCl4 in CH2Cl2 HCI CH3 CH3

An Acylation CH3 CH3 C H3 C H2 C H2 C H2 CCl O TiCl 4 in CH2 C l2 CCH2 CH2 CH2 CH3 CH3 O CH3 + HCl

Friedel-Crafts Alkylation many more limitations R RX,AICI3 HCI

Friedel-Crafts Alkylation many more limitations RX, AlCl 3 R + HCl

Friedel-Crafts alkylation H R Lewis acid +R一X +H一X (AICl.FeBr3,etc.) (X CI,Br,I) CH3 CH3 C一 CH3 CH3-C-CI CH; +HCI CH benzene t-butyl chloride t-butylbenzene (90%)

Mechanism CH3 CH3 CH3-C-CI AICl3± CH;-C@ AICI CH; CH; t-butyl carbocation CHS产Q (CH):C. CH3- CH ⊕ resonance stabilized intermediate C户AICh (CH3);C +HCI (+AIC13)

Mechanism C H3 C CH3 CH3 Cl AlCl 3 C CH3 CH3 C H3 t-butyl carbocation AlCl 4 C H3 C CH3 CH3 (CH3) 3C H (CH3 ) 3C (CH3) 3C resonance stabilized intermediate C l AlCl 3 (CH3) 3C + HC l (+ AlCl 3)