tareek Posted March 2 Share Posted March 2 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 Link to comment Share on other sites More sharing options...
chenbeier Posted March 2 Share Posted March 2 (edited) 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 by chenbeier Link to comment Share on other sites More sharing options...
exchemist Posted March 2 Share Posted March 2 (edited) 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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 Something has gone wrong with your post. Edited March 2 by exchemist Link to comment Share on other sites More sharing options...
tareek Posted March 2 Author Share Posted March 2 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 Link to comment Share on other sites More sharing options...
chenbeier Posted March 2 Share Posted March 2 (edited) 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 by chenbeier Link to comment Share on other sites More sharing options...
tareek Posted March 2 Author Share Posted March 2 Because we only have 2 equivalents of Grignard Link to comment Share on other sites More sharing options...
chenbeier Posted March 2 Share Posted March 2 (edited) 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 by chenbeier Link to comment Share on other sites More sharing options...
exchemist Posted March 2 Share Posted March 2 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. Link to comment Share on other sites More sharing options...
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