2 Pinacolic Rearrangement CH3 CH3H+ CH2c--C-chr= CH CH3 -H,O OH OH OH+OH, CH 3 H3(H→CHy CH3-CH -C-C-CH OH CH +OH CH O CH3
2 Pinacolic Rearrangement CH3 C CH3 OH C CH3 CH3 OH H + H2 O CH3 C CH3 OH C CH3 CH3 +OH2 CH3 C CH3 OH C CH3 CH3 + CH3 C CH3 OH C CH3 CH3 + H + CH3 C CH3 O C CH3 CH3
The stable cation formed superior PhC—C 2-> Ph2C- OH OH OH Ph2CH-CH PhocH-ch OH -H Phenyl group move first PhHC—CHPh PhHC—CHPh一 OHOH Ph,CH-CH tOu -u+ Ph,Ch-CH
The stable cation formed superior H + Ph2 C OH CH2 OH + Ph2 C CH2 OH H + Ph2 CH CH +OH Ph2 CH CH O Phenyl group move first PhHC OH CHPh OH H + PhHC CHPh OH + Ph2 CH CH O H + Ph2 CH CH +OH
Phenyl with electron donor group move first (p-Meoc6 -CPh 72% H (p-MeoC Ha)C-CPhy Ph o OHOH p-Meoc6H4c--cph? 28% O C6HgOMe-p
Phenyl with electron donor group move first (p MeOC6H4 ) 2C OH CPh2 OH H + (p MeOC6H4 ) 2 C Ph CPh O p MeOC6H4 C O CPh2 C6H4OMe p 72% 28%
Under Hno2. the amino alcohol rearranges as that of pinacol NH 2 HNO2 CHO OH CH N HNO oH
Under HNO2, the amino alcohol rearranges as that of pinacol HNO2 HNO2 NH2 OH CH2 NH2 OH O CHO
3 a-Ethandione rearrangement Naoh COoNa h,+ COOH Ph-C-C-Ph Etoh Phc Phc OH OH O OH Ph-c-c-Ph= Ph-C-C-0 Ph-c-C=0 Ph OH O Ph-C—C=0 Ph
3 α-Ethandione Rearrangement Ph C C Ph O O NaOH EtOH Ph2 C COONa OH H3O + Ph2 C COOH OH Ph C C Ph O O OH - Ph C C Ph O OH O - Ph C C Ph O OH - O Ph C C Ph OH O - O