Question

1- Why is Ortho nitrobenzoic acid more acidic than Ortho hydroxybenzoic acid
2- explain why Ortho bromobenzoic acid is more acidic than Ortho bromopropanoic acid

Answer 1

1.The -M effect of NO2 will stabilize the electron density of conjugate anoin (base). From that logic also, since NO2 is ewg and OH is edg, o-nitrobenzoic acid is more acidic than o-hydroxybenzoic acid.

2.Hence, nitro group on ortho position has higher inductive effect compared to the nitro group on para position. Therefore, more liberation of H+ is causes the acidity of a compound. Hence, , o-nitrobenzoic acid is more acidic compared to p-nitrobenzoic acid.

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