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Give the migratory order for pinacol pinacolone reactions?

Give the migratory order for pinacol pinacolone reactions?

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1 Answers

Bhavya
askIITians Faculty 1281 Points
8 years ago

In the pinacol rearrangement, a 1,2-diol is treated with acid and rearranges to a carbonyl compound in the following manner :

505-2301_pinacol rearrangement.PNG

migratory aptitude of groups in pinacol-pinacolone rearrangement is:

H>Ph>Me3C>MeCH2>Me

The reason this kind of migration occurs are:-
1) help stabilize the developing carbocation center
2) once fully migrated, produces a resonance stabilized hydroxyl-carbocation.

Generally, both hydroxyls will protonate and lead to separate products. In terms of which group will migrate, the only thing agreed upon is that a tertiary carbon will migrate in preference to a secondary carbon which will migrate in preference to a primary carbon.Clearly, the ability of the migrating group to stabilize positive charge plays a role.

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