Grignard with benzoic acid

[tareek]

How do 2 equivalents Grignard react with benzoic acid. The first one will deprotonate the acid proton. But will the second one attack the carboxylat ?

By the way we are using a weak acid 

[chenbeier]

Carbonic acids cannot be treated with Grignard

https://upload.wikimedia.org/wikipedia/commons/thumb/5/53/Grignard_with_carbonyl.png/450px-Grignard_with_carbonyl.png

You can see they also treated CO2 to make carbonic acid. This would be not possible if carbonic acid would under go Grignard.

Edited March 2, 2024 by chenbeier

[exchemist]

1 hour ago, tareek said:

How do 2 equivalents Grignard react with benzoic acid. The first one will deprotonate the acid proton. But will the second one attack the carboxylat ?

By the way we are using a weak acid 

Carboxylate anions are not very strongly electrophilic, if I remember correctly. What do you think will happen?

2 minutes ago, chenbeier said:

Carbonic acids cannot be treated with Grignard

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Edited March 2, 2024 by exchemist

[tareek]

1 hour ago, exchemist said:

Carboxylate anions are not very strongly electrophilic, if I remember correctly. What do you think will happen?

Something has gone wrong with your post.

I dont know i would say the benzoic acid, will be formed back. But are you sure Acetophenon can't forn

[chenbeier]

If so why should it stop at acetophenon, this could react to 2 Phenyl-2-propanol. But it doesn't happen. If you use instead of the acid the ester then its possible.

 

Edited March 2, 2024 by chenbeier

[tareek]

Because we only have 2 equivalents of Grignard

[chenbeier]

Why do you think it will not stop.

If it works it will go through, even you have only two equivalent. Then some reactant will be left.

 

Edited March 2, 2024 by chenbeier

[exchemist]

33 minutes ago, tareek said:

I dont know i would say the benzoic acid, will be formed back. But are you sure Acetophenon can't forn

The problem, as @chenbeier says,  is that a carbonyl group will react with a Grignard reagent much faster than a carboxylate. So any acetophenone produced would immediately react in preference to the remaining carboxylate. I’m not sure whether a carboxylate anion will react at all with a Grignard reagent. Nucleophilic attack on an anion seems like a bit of an uphill struggle, though it’s true most of the -ve charge will be on the O atoms.