Grignard and Carboxylic acid

[JustwantDDS]

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What happens here?
can someone link me something so i can look at it

i tried searching but couldnt really get what i was looking for

 

[toothhornet88]

What happens here?
can someone link me something so i can look at it

i tried searching but couldnt really get what i was looking for

http://www.mhhe.com/physsci/chemist...arey04oc/ref/ch19reactioncarboxylicacids.html
go where it says Preparation of Carboxylic Acid Derivatives and look where it has a carboxylic acid reacting with a base...well that's what happens when grignard reacts with a carboxylic acid. Plus if you have more than one mole of Grignard it will latch on to the O- to become O-MgX

 

[Demps]

I think you get two rounds of nucleophilic attack on the carbnoyl and end up with a tertiary alcohol

 

[Clancyp]

I think you get two rounds of nucleophilic attack on the carbnoyl and end up with a tertiary alcohol

Usually its the same with esters too.

 

[needzmoar]

What happens here?
can someone link me something so i can look at it

i tried searching but couldnt really get what i was looking for

The grignard and a carboxylic acid is a wasteful acid base reaction. I believe you and the posters above are looking for the organolithium reagent with a carboxylic acid followed by hydrolysis to form a ketone. That's one of the key differences between organolithium reagent vs the grignard.

edit: here's a link http://www.orgsyn.org/orgsyn/prep.asp?prep=cv5p0775

essentially it's just 2 molar eq of RLi + carboxylic acid followed by acidic hydrolysis

 

[PooyaH]

I think you get two rounds of nucleophilic attack on the carbnoyl and end up with a tertiary alcohol

That would be the case with esters, which is called sapofinication (ester hydrolysis by a strong base), but Gringard always reacts with the most acidic hydrogen first. So in case of carboxylic acid, it would make a carboxylate.