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Topic: carboxylic acid with LDA  (Read 4899 times)

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Offline aviad

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carboxylic acid with LDA
« on: November 15, 2014, 09:32:04 AM »
hi
i have a question when you react a carboxylic acid with LDA base will it take the proton to make the ion or the alpha proton im not sure due to the fact LDA fever the kinetic product 
the question itself is what is the proudect  of two aquvelant of hexanoic acid with 2 LDA and 1 etyil bromide
thank you.

Offline orgopete

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Re: carboxylic acid with LDA
« Reply #1 on: November 15, 2014, 10:45:06 AM »
Why are they using two equivalents? Isn't that a clue?
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline asmcriminal

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Re: carboxylic acid with LDA
« Reply #2 on: November 18, 2014, 10:25:13 PM »
LDA attacks the beta hydrogen.

Offline Altered State

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Re: carboxylic acid with LDA
« Reply #3 on: November 19, 2014, 03:56:48 AM »
LDA attacks the beta hydrogen.

Don't think so
It will start removing the -CO2H proton

Offline asmcriminal

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Re: carboxylic acid with LDA
« Reply #4 on: November 19, 2014, 09:56:17 AM »
LDA attacks the beta hydrogen.

Don't think so
It will start removing the -CO2H proton

Yeah, i feel dumb, I don't know what i was thinking. Everything I said was wrong in my last post. But yeah, it will attack the H on the oxygen, that oxygen is resonance stabilized making it easier to deprotenate.

Offline debabrata

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Re: carboxylic acid with LDA
« Reply #5 on: December 10, 2014, 08:11:21 AM »
shouldn't  2nd equivalent LDA attack alpha H after abstructing the carboxylic proton?

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