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What is the preference order of the 1,2 methyl, hydride and phenyl shifts during the time of rearrangements ??? Why is it so ?
Dear Swapnil,
Many factors must be considered when analyzing the course of a pinacol rearrangement. These include:
• Which hydroxyl group is lost as water? or Which intermediate carbocation is more stable?• What is the inherent shifting tendency (migratory aptitude) of different substituent groups?• What is the influence of steric hindrance and other strain factors on the rearrangement?• Are epoxides formed as intermediates in the pinacol rearrangement?• Does product stability govern the outcome of competing rearrangements?• Do the reaction conditions (i.e. type of acid, concentration, solvent and temperature) influence the course of rearrangement?
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