Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: J1800 on January 30, 2013, 12:27:21 AM

Title: Why are different oxygens acting as nucleophiles in these reactions?
Post by: J1800 on January 30, 2013, 12:27:21 AM
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2FCbYhlCo.png&hash=bf40346c64af8e643f1f60479084c445)
Title: Re: Why are different oxygens acting as nucleophiles in these reactions?
Post by: orgopete on January 30, 2013, 08:30:35 AM
It depends on the drawer and, because of resonance, the electrons are virtually equivalent. I know the proton resides in different positions in the intermediates of each, but because proton transfers are very fast, their position is difficult to measure. If we wanted to be particular, I would argue the second example is preferred as the electrons of an sp3 oxygen are more basic than those of the sp2.