Which of the following would you predict to be the stronger acid?
(a) Benzoic acid or para-nitrobenzoic acid
(b) $C H_{3} - C H_{2} - C H_{2} - O H$ or $C H_{3} - C H = C H - O H$
(c) $C H_{3} - C H = C H - C H_{2} - O H$ or $C H_{3} - C H = C H - O H$

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Solution

(a) Paranitro benzoic acid is more acidic because we know that electron withdrawing group at ortho or para position increases acidity of the aromatic benzoic acid. $N O_{2}$ group is an electron withdrawing group.

(b) Second one is more acidic because it undergoes resonance and makes the conjugate base stable and hence more acidic.

(c) Second one is more acidic because the conjugate base it undergoes resonance.

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