Acylation occurs ortho to oH possible complexation CH3 via H bond CH3 CHO
Acylation occurs ortho to OH O H O O CH3 CH3 CH3 O O O + + possible complexation via H bond
Gatterman-Koch Formylation CH CO,HCI AIC13/CuCl benzene or activated benzene needed in situ preparation of formyl chloride 0 C=0+HCI HCCI
Gatterman-Koch Formylation CO, HCl AlCl 3/CuCl CH O benzene or activated benzene needed HCCl O C O + HCl in situ preparation of formyl chloride
Oxymercuration Hydration Markovnikov OH CH;CH2C=CH Hes0H,s04→ H20 CH;CHC-CH an enol CH:CH2CCH3 a ketone
Oxymercuration Hydration Markovnikov C H3 C H2 C CH HgSO4 , H2 SO4 H2 O C H3 C H2 C=CH2 OH an enol C H3 C H2 CCH3 O a ketone
Hydroboration Hydration Anti-Markovnikov OH CH3CH2C≡CH 1)disiamyl borane CH3CH2CH-CH2 2)H2O2,NaOH an enol CH:CH2CHCH (sia)2BH an aldehyde
Hydroboration Hydration Anti-Markovnikov 2) H2 O2, NaOH 1) disiamyl borane O C H3 C H2 C H2 C H C H3 C H2 C CH an enol OH C H3 C H2 CH=CH2 (sia) an aldehyde 2 B H B H
Ozonolysis Alkene Cleavage CH3 1)O3 in CH2C12 CH3> CH3 C=0+0=C CH; 2)CH3SCH3 DMSO or Zn/HOAc CH3 DMS 呢 ozonide
Ozonolysis Alkene Cleavage C=C CH3 CH3 CH3 H O3 in CH2C l2 C O H CH3 C CH3 CH3 + O H CH3 CH3 CH3 C=C O O O 1) 2) CH3 SCH3 or Zn/HOAc O O O H O O O H ozonide DMS + DMSO