δ H2C=C+CH2 HC CH2C(CH3)2(not CICH2 CH(CH3)2 CH3 H CI 2-Methylpropene tert-Butyl chloride Cl CH3 C 8+δ + hcl Methylevclohexene 1-Chloro-l-Methylcyclohexane
H2C C + HCl CH2C(CH3 ) 2 H Cl (not ClCH2CH(CH3 ) 2 CH3 2-Methylpropene tert-Butyl chloride − + − + CH3 CH3 + HCl Cl CH3 H Methylcyclohexene 1-Chloro-1-Methylcyclohexane − + − +
2. The stabilities of carbocation (碳阳离子的稳定性解释马氏规则) a CI b CH3CHCH2H- CH3 CHCICH 2C Markovnikov addition product Stable H3C—c=cH2+ H b Cl Ch2cHCH CHCH, CH,C Anti-Mar's rule Unstable
2. The Stabilities of carbocation （碳阳离子的稳定性解释马氏规则） C H CH2 + H-Cl CH3CHCH2H Markovnikov addition product H3C + b a CH3CHCH2 + Cl - CH3CHClCH3 2 o C + Cl - CH3CH2CH2Cl 1 Anti-Mar's Rule o C + Stable Unstable 2 o C + 1 o C + a b H
The stabilities of carbocation CH CH3 C b CH2CCH,H CH3CCICH3 30C Markovnikov addition product Stable 3c—C=cH2 H-CI CH CH. CH3CCH CI CH3 CHCH,CI CH3 Anti-Mar's Rule 3°C+S1°C Unstable
The Stabilities of carbocation C CH2 + H-Cl CH3CCH2H Markovnikov addition product H3C + b a CH3CCH2 + Cl - CH3CClCH3 3 o C + Cl - CH3CHCH2Cl Anti-Mar's Rule 1 o C + Stable Unstable 3 o C + 1 o C + a b H CH3 CH3 CH3 CH3 CH3
Mar's Rule help us to predict the outcome of the addition reaction C=C+CH,+ HCI- CH2C(CH3)2 (not CICH,CH(CH3) CH3 H CI 2-Methy pRopene tert-Butyl chloride Major product H2C=C+CH3 I-Cl- Ch2C(CH3)2 (not CICH2CI(CH3)2 CH3 C 2-Methylpropene 2-Chloro-1-iodo-2-methylpropane (Major product)
Mar’s Rule help us to predict the outcome of the addition reaction H2C C + HCl CH2C(CH3 ) 2 H Cl (not ClCH2CH(CH3 ) 2 CH3 2-Methylpropene tert-Butyl chloride − + − + CH3 Major Product H2C C + I-Cl CH2C(CH3 ) 2 I Cl (not ClCH2CI(CH3 ) 2 CH3 2-Methylpropene 2-Chloro-1-iodo-2-methylpropane − + − + CH3 (Major product)
9. 2D An exception to Markovnikov's rule (马氏规则例外) The addition of HBr to alkenes, it is Only when HBr is used in the presence of peroxides(ROOR), it is an exception to Mar' ruter CH3 CH,CH, Br Major product CH3CHCH, HBr Free radical reaction CH3 CHBrCH3 Mar's product Ionic reaction
9.2D An exception to Markovnikov’s Rule (马氏规则例外） The addition of HBr to alkenes, it is Only when HBr is used in the presence of peroxides (ROOR), it is an exception to Mar’ Rule. CH3CH=CH2 + HBr ROOR CH3 CH2 CH2 Br Major product CH3 CHBrCH3 Mar's product Ionic reaction Free radical reaction