Comparing (a) and (b), which of the following statement(s) is/are correct?
A
Both (a) and (b) shows ortho effect
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B
(b) is more acidic than (a)
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C
Conjugate base of (b) is stabilised by hydrogen bonding
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D
(a) is more acidic than (b)
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Solution
The correct option is D (a) is more acidic than (b) In general, whenever a group is present at the ortho position of benzoic acid, irrespective of its nature (EDG or EWG), it increases the acidic strength as compared to benzoic acid itself. This effect is called ortho effect. Hence, statement (a) is correct.
Steric Inhibition of Resonance (SIR) and Electronic factor, both contributes to the ortho effect.
Comparing (a) and (b):
The conjugate base of A is more stable as compared to the conjugate base of B since H-bonding stabilises the anion in the former one.
Compound (b) does not form H-bonding so it is least acidic compare to (a).