Conversion of 1,2-glycols pinacol to ketone or aldehyde pinacolone by means of acid is called pinacol-pinacolone rearrangement. Its mechanism is as follows-. Note:Migration of alkyl group and elimination of -OH by the proton catalyst take place simultaneously. The migrating group migrates within the molecule. When a mixture of two different pinacols are heated in the present of acid , no cross product is formed. Share on Facebook.
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Pinacol Pinacolone Rearrangement
The pinacol—pinacolone rearrangement is a method for converting a 1,2-diol to a carbonyl compound in organic chemistry. The 1,2-rearrangement takes place under acidic conditions. The name of the rearrangement reaction comes from the rearrangement of pinacol to pinacolone. This reaction was first described by Wilhelm Rudolph Fittig in of the famed Fittig reaction involving coupling of 2 aryl halides in presence of sodium metal in dry ethereal solution. In the course of this organic reaction , protonation of one of the —OH groups occurs and a carbocation is formed. If both the —OH groups are not alike, then the one which yields a more stable carbocation participates in the reaction.
30.2: Pinacol Rearrangement
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