Organic Chemistry Basics 2 Question 34

34. HOOC

The product $A$ will be

(2003)

(a)

(b)

(c)

(d)

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Solution:

  1. In general, the order of acid strength is

$-\mathrm{C} \equiv \mathrm{CH}<\mathrm{ROH}<\mathrm{H}_{2} \mathrm{O}<\mathrm{PhOH}<R-\mathrm{COOH}$

Therefore, during stepwise neutralisation of given acid, $-\mathrm{COOH}$ will be neutralised first.

In the second step, the phenolic $-\mathrm{OH}$, assisted by $-I$ effect of $-\mathrm{NO}_{2}$ at meta position will be neutralised.