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Pinacol-Pinacolone Rearrangement

1) The pinacol-pinacolone rearrangement is an acid-catalyzed rearrangement of vicinal diols (pinacols) to methyl ketones (pinacolones). 2) The reaction proceeds through either a carbocation intermediate or a single step involving generation of the carbocation and elimination of the leaving group. 3) It can be viewed as a "push-pull" effect, where the oxygen lone pair pushes the migrating group as elimination of the leaving group pulls it to the electron deficient carbon center.

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Subhro Chatterjee
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627 views10 pages

Pinacol-Pinacolone Rearrangement

1) The pinacol-pinacolone rearrangement is an acid-catalyzed rearrangement of vicinal diols (pinacols) to methyl ketones (pinacolones). 2) The reaction proceeds through either a carbocation intermediate or a single step involving generation of the carbocation and elimination of the leaving group. 3) It can be viewed as a "push-pull" effect, where the oxygen lone pair pushes the migrating group as elimination of the leaving group pulls it to the electron deficient carbon center.

Uploaded by

Subhro Chatterjee
Copyright
© © All Rights Reserved
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PINACOL-PINACOLONE REARRANGEMENT

The above reaction is known as pinacol-pinacolone rearrangement .


Pinacol is basically a 1,2-diol or we can say that it is a vic-diol and
pinacolone is methyl-ketone. This is basically a acid catalysed
rearrangement .
In the mechanism of this rearrangement reaction we show two types of
mechanistic course of the reaction. i.e. we have shown the mechanistic
course in which reaction passes through carbocataion intermediate on
the other hand we have shown also that mechanistic course in which
generation of carbocataion and the elimination of the leaving grp.
Occurs ia single step .
We can view this rearrangement as a “push” “pull” effect i.e.
elimination of leaving group pulls the migrating group where as
oxygen lone-pair pushes it.
In this rearrangement reaction there is a migration of the migrating
group to the electron deficient carbon centre.
MECHANISM

2ND PATHWAY
The order of migratory aptitude will be as followes
Explain the above observation.

Another example of this rearrangement is as followes-

Write down the mechanistic course of the above reaction.

ANS. OF THE 2 QUESTIONS GIVEN AT THE END


We have the following conversion

In case of epoxied we have the following observation.

Mechanistic course is as followes


ANOTHER INTERESTING OBSERVATION

This reaction is known as PINACOLIC-DEAMINATION


INTERESTING OBSERVATION

CONVERSION

ANS.
HOW CAN YOU CONVERT GLYCEROL INTO ACROLEIN ?
PROBLEM

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