Carbocation Rearrangement With Ring Contraction/ Pinacol-Pinacolon Rearrangement (with an example)
Автор: Mayya Alocci
Загружено: 2021-11-30
Просмотров: 1990
Pinacol-Pinacolon rearrangement is when a diol turns into a carbonyl with the use of an acid.
In this rearrangement the starting material must have two alcohol groups next to one another. Under acidic condition, the OH of one of the alcohols get protonated to become OH2+. OH2+ is a good leaving group and leaves in the next step, creating a carbocation (C+). Once carbocation is created, we can think of rearrangements. We must look at the carbon neighboring the carbocation (in this case the one with the OH group). One of the carbon bond from the neighboring carbon moves to the carbocation. An easy way to draw the product is to draw the reactant and erase the bond that broke off and add the bond that was created. The carbon with OH that lost the bond becomes the new carbocation. Now, we just need to move the electrons from the oxygen to the carbocation to make C=O-H+, followed by deprotonation (removal of hydrogen).
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