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Why electrophilic substitution in benzoic acid takes place at meta position?

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First of all,electrophillic substitution reaction means the replacement of any of the atoms of a parent compound by an electrophile. Now,electrophiles are electron loving species i.e.,they always attack at the region of maximum electron density. Again,if you draw the structure of benzoic acid,you will...
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First of all,electrophillic substitution reaction means the replacement of any of the atoms of a parent compound by an electrophile.

Now,electrophiles are electron loving species i.e.,they always attack at the region of maximum electron density.

Again,if you draw the structure of benzoic acid,you will find that the pi electrons of carbonyl group of COOH is in conjugation (alternate single and double bonds) with the pi electrons of the benzene ring. As a result the pi electrons are delocalised (they move from their original positions )resulting into a number of structures which are in equilibrium with each other.(These structures are easy to draw.you can find them in almost every good chem textbook).You will find that in each of those structures,either the ortho carbon or the para carbon acquires a positive charge. It is only the meta carbon that doesn't acquire positive charge. That is,electron density always remain maximum at the meta position. So it is quite natural that electrophile will always attack at the meta position……

This is the reason why electrophillic substitution in benzoic acid always occurs at the meta position.

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