[sotirone]

Hello!

I am studying for my Organic Pharmaceutics Chemistry lesson and my professor likes to ask random questions.

A question that has been asked in the past is: Which of p- or m- nitrobenzoic acid is more acidic and why?

I am really lost here in trying to make out the answer.

[chenbeier]

Write down the mesomeric structures and compare.

[sotirone]

Write down the mesomeric structures and compare.

I did, one of the para product's mesomeric structures has the carbocation of the ring placed on the 1 position (the position of the carboxylic acid group) while the mesomeric structures of the meta product have the carbocation of the ring on the left or right (positions 2 or 6) of the ring.

Does the positive charge of the no1 carbocation help (due to induction) the release of the hydrogen of the carboxylic group? Is that the answer I am looking for?

[chenbeier]

I would say so.

[sotirone]

I would say so.

Great, thanks!