Which of the following has the maximum acidic strength?a)o-Nitrobenzoi...
Ortho isomer is the strongest one because in this case --- 1.ortho effect..2... the -I effect of the -No2 grp is the most powerful because distance from the -COOH grp is minimum ...3...the corresponding Carboxylic ion is stabilised by intramolecular electrostatic interaction between the carboxyl and the nitro group...So...the correct answer is option A..
Which of the following has the maximum acidic strength?a)o-Nitrobenzoi...
The acidic strength of a compound is determined by the stability of the conjugate base formed when the compound loses a proton. The more stable the conjugate base, the stronger the acid. In this case, we are comparing three different isomers of nitrobenzoic acid (o-, m-, and p- isomers) and p-nitrophenol.
1. o-Nitrobenzoic acid:
- In the o-isomer, the nitro group (-NO2) is attached to the benzene ring in the ortho position, which is adjacent to the carboxylic acid (-COOH) group.
- The negative charge of the conjugate base formed after the loss of a proton is delocalized between the carboxylate group and the ortho position of the benzene ring.
- This delocalization of the negative charge stabilizes the conjugate base and increases the acidic strength of o-nitrobenzoic acid.
2. m-Nitrobenzoic acid:
- In the m-isomer, the nitro group is attached to the benzene ring in the meta position, which is not directly adjacent to the carboxylic acid group.
- The negative charge of the conjugate base formed after the loss of a proton is not delocalized as effectively as in the o-isomer.
- Therefore, m-nitrobenzoic acid is less acidic than the o-isomer.
3. p-Nitrobenzoic acid:
- In the p-isomer, the nitro group is attached to the benzene ring in the para position, which is not directly adjacent to the carboxylic acid group.
- Similar to the m-isomer, the negative charge of the conjugate base formed after the loss of a proton is not delocalized as effectively as in the o-isomer.
- Therefore, p-nitrobenzoic acid is also less acidic than the o-isomer.
4. p-Nitrophenol:
- In p-nitrophenol, the hydroxyl group (-OH) is attached to the benzene ring in the para position, and the nitro group is attached to the phenol ring.
- The presence of the hydroxyl group increases the stability of the conjugate base by resonance delocalization of the negative charge.
- Therefore, p-nitrophenol is more acidic than the p-nitrobenzoic acid isomers.
In summary, among the given compounds, o-nitrobenzoic acid has the maximum acidic strength due to the effective delocalization of the negative charge in its conjugate base.
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