Question

C. Interestingly, when compared to benzoic acid, p-methoxybenzoic acid is less acidic and m- methoxybenzoic acid is more acidic. Please explain how the location of the methoxy groups influences the pka of each isomer relative to benzoic acid using drawings and a minimum amount of words. TIP: How stable is each conjugate base? What is or isn't stabilizing it? TIP #2: EAS/Aromaticity has nothing to do with it. Meo OME increasing acidity

Answer 1

* Presence of electodonalinger on the bengene ring will decreases the acidity of compound. * presence of electron with drawing group on the benzene ring will increases the acidity of composand. LOH methoxy group is para to carboxylic and this interm decreases the electrons dependence of oxygen atoon on hydrogen. so, the rate of loss of hydrogen atom decreases and causes the decrease in acidity. a presence of methoxy group meta to carboxylic auld has no effect, so that acidic effect will be normal and has higher than the p-methoxy benzoic acid. a y ö- This resonance effect will - decreases the cocidity of O acidic protes on Carboxylic acid group. * Acidity increases from p-methoxybenzoic acid to benzoic aud. which is more. * Audity is more for m mettory benzoic acid than that of benzoic acid.