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Topic: mechanism esterification  (Read 1691 times)

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Offline mannaia

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mechanism esterification
« on: April 08, 2013, 10:57:22 AM »
Hello,
sorry for the basic question.

Why during esterification of a carboxylic acid (conducted in acidic medium), the oxygen of the carbonyl group is protonated ? Why not the oxygen of the -OH group.
This is what is always shown as the first step of the reaction mechanism.

Thanks in advance for any help

Kind regards
mannaia
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Offline Dan

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Re: mechanism esterification
« Reply #1 on: April 08, 2013, 11:37:15 AM »
Consider the relative stabilities of the protonated acids.

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Offline mannaia

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Re: mechanism esterification
« Reply #2 on: April 08, 2013, 01:05:56 PM »
OK thanks, actually when the carbonyl is protonated, the overall structure benefits from a strong stabilization by resonance (that makes possible the displacement of the positive charge onto the carbon of the carbonyl).
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