One or more options correct
Choose the correct statement(s) about acidity and basicity of organic compounds (aqueous solution, ).
- A. The basic strength follows the order .
- B. -Nitrophenol is a stronger acid than -nitrophenol.
- C. -Methoxybenzoic acid is a stronger acid than benzoic acid because of the effect of the methoxy group on the carboxylate.
- D. -Nitrobenzoic acid is a stronger acid than -nitrobenzoic acid.
Show answer and solution
Answer: A, D
(A) True. In water, alkyl groups raise basicity by their effect, but solvation of the ammonium ion (fewest N-H bonds in the tertiary ion) and steric crowding offset this for the tertiary amine; the observed values are about 3.27, 3.38, 4.22 and 4.75 for dimethylamine, methylamine, trimethylamine and ammonia respectively. (For the ethylamines the order is different, .)
(B) False. The -nitro group stabilises the phenoxide by resonance (the negative charge reaches the nitro group), whereas the meta group acts only inductively. Hence -nitrophenol () is more acidic than -nitrophenol ().
(C) False. The effect of at para destabilises the carboxylate, so the acid is weaker ( against for benzoic acid).
(D) True. The ortho effect (steric twisting of out of the ring plane plus the strong of a close nitro group) makes the ortho isomer () stronger than the para isomer ().
Correct options: (A) and (D).
(B) False. The -nitro group stabilises the phenoxide by resonance (the negative charge reaches the nitro group), whereas the meta group acts only inductively. Hence -nitrophenol () is more acidic than -nitrophenol ().
(C) False. The effect of at para destabilises the carboxylate, so the acid is weaker ( against for benzoic acid).
(D) True. The ortho effect (steric twisting of out of the ring plane plus the strong of a close nitro group) makes the ortho isomer () stronger than the para isomer ().
Correct options: (A) and (D).
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