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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 ?

What is the preference order of the 1,2 methyl, hydride and phenyl shifts during the time of rearrangements ??? Why is it so ?

Grade:11

1 Answers

Aman Bansal
592 Points
9 years ago

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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