In the pinacol rearrangement, a rearrangement occurs between two tertiary carboc
ID: 509068 • Letter: I
Question
In the pinacol rearrangement, a rearrangement occurs between two tertiary carbocations. If both the initial and the rearranged carbocations are tertiary, what is the driving force for this rearrangement?
The rearranged carbocation is substituted by a tert-butyl group.
The initially formed carbocation is destabilized by the hydroxy-containing alkyl group (O is inductively withdrawing).
The final carbocation is O-substituted and resonance stabilized.
The rearranged carbocation is substituted by a tert-butyl group.
The initially formed carbocation is destabilized by the hydroxy-containing alkyl group (O is inductively withdrawing).
The final carbocation is O-substituted and resonance stabilized.
Explanation / Answer
option C) The final carbocation is O-substituted and resonance stabilized is the correct answer.
The electron density from oxygen atom are transferred to carbocation and stabilized through resonance.
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