Monday, 3 October 2016

organic chemistry - Migratory aptitude in pinacol-pinacolone rearrangement


I am confused about the migratory aptitude of various groups, as there are many different orders for the same given in different places, especially about -Ph and -H. I would like to know if someone could reliably tell the order.



Answer




According to my FIITJEE (a coaching institute in India) textbook, the relative order of migratory aptitude of groups in pinacol-pinacolone rearrangement is:


$$\ce{H > Ph > Me_3C > MeCH_2 > Me}$$


There does not seem to be a direct correlation between the mass and the migratory aptitude of these groups.


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