One or more options correct
Which of the following comparisons regarding acid/base strength is (are) correct?
- A. -Nitrophenol is a stronger acid than phenol.
- B. -Nitroaniline is a weaker base than aniline.
- C. Benzoic acid is a weaker acid than -methylbenzoic acid.
- D. Acetic acid is a stronger acid than chloroacetic acid.
Show answer and solution
Answer: A, B
(A) Correct. The -nitrophenoxide ion is stabilised by delocalisation of the negative charge onto the nitro group through resonance (, ), so compared with about for phenol. (B) Correct. The lone pair of nitrogen in -nitroaniline is pulled into the ring and the nitro group by the effect, so it is less available for protonation; the conjugate acid has against for anilinium. (C) Incorrect. The methyl group is electron donating (, hyperconjugation) and destabilises the carboxylate, so -toluic acid () is weaker than benzoic acid (); benzoic acid is the stronger one. (D) Incorrect. The effect of chlorine stabilises the carboxylate, so chloroacetic acid () is stronger than acetic acid (). Answer: A and B.
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