What is the product of rxn:
1-Bromo-2-Methyl Benzene --------------> ?????
Mg/ether
CO2/H3O+
KMnO4/OH-
H+
is it para-methyl benzoic acid?
Well the ques. was that what would be the product of the rxn. if Ortho-Bromo Toluene is treated with the earlier given reagents.
And the options are:
a) Ortho-Hydroxy Benzoic Acid
b) Othro-Methyl Phenol
c) Benzoic acid
d) Benzene
It came in one of my chem tests and i will not be having the answer before 1 week.
And the options are:
a) Ortho-Hydroxy Benzoic Acid
b) Othro-Methyl Phenol
c) Benzoic acid
d) Benzene
It came in one of my chem tests and i will not be having the answer before 1 week.
well, i believe its (c)benzoic acid
reactions:
ortho-bromo toluene with MgBr will give methyl phenyl magnesium bromide which on treatment with co2 and subsequent hydrolysis will give methyl benzoic acid. methyl benzoic acid on strong oxidation(KMno4) will give 1,2-benzene dioc acid which reacts with H+ eliminating co2 finally leaving us with benzoic acid. please tell me if i'm right....
reactions:
ortho-bromo toluene with MgBr will give methyl phenyl magnesium bromide which on treatment with co2 and subsequent hydrolysis will give methyl benzoic acid. methyl benzoic acid on strong oxidation(KMno4) will give 1,2-benzene dioc acid which reacts with H+ eliminating co2 finally leaving us with benzoic acid. please tell me if i'm right....
Well, I also got the same answer. I still do not know the right answer till 1 or 2 more weeks. It came in one of my exams. But, i and my friends had a controversy over whether H+ will remove CO2 or not. Is it a standard treatment or r u guessing???
Hi Ankul! As far as I know, carboxylic acids undergo decarboxylation only when the final products formed are more stable than the initial ones. Isn't 1,2- benzene dioic acid more stable than benzoic acid?
I have the same confusion in this question.... since 1,2- benzoic acid isn't in the choices given... i can think of Benzoic acid as the only possible answer.
Hi all... well there was a misprinting in this ques. in my exam... instead oh H+ it had to be soda lime... and the answer given is Benzene.. Well can anybody tell me how will that change in the question give Benzene as the answer???
Hi ankul,
hope you are fine!!! i didnt notice this qn otherwise i would have replied earlier, so sorry for the delay!!! the first step results in a grignard reagent which when combines with carbondioxide forms an acid !!! so after the 2nd step the product is 2 methyl benzoic acid!!! when reacted with KMnO4 the methyl part gets oxidised to give a dicarboxylic acid(benzene with COOH at 1,2 positions-can you please give its IUPAC name)!!! this reacts with excess of soda lime to give benzene- both the acid parts undergo decarboxylation!!! hope you get it and if i am wrong somewhere please correct me!!! kvs
Yeah i got it now. But actually i wasn't getting the correct answer in my exam as there was a misprinting. Instead oh sodalime it was H+ given as last step. So... couldn't proceed further. The dicarboxylic acid is popularly known as Pthalic acid. Its IUPAC name should be Benzene-1,2-dioic acid.... Dont u think so...???
Well u seem to b correct!!! the IUPAC name sounds correct to me!! my nomenclature is a bit weak in aromatic compounds!!! urs sounds strong.......kvs