Question

Question 4 0.5 pts Which of the following molecules will have the highest acidity? • Previous Next >

Answer 1

Compound D has highest acidity.

We know that higher the stability of the conjugate base higher will be the acidity of the compound. After removal of acidic proton from the compound D ( benzoic acid), the negative charge will be on the more electronegative oxygen atom and the conjugate base has two equivalent resonance structures.

In case of compound A and C, charge separation take place in the resonating structure of the corresponding conjugate bases.

The negative charge will be generated on the less electronegative carbon atom for the conjugate base of compound B.

So conjugate base of compound D is more stable than the others .

So the acidity of the compound D is highest.

(conjugate bone) (Aromaticity is lost). (B) ( Н -- - ( conjugate base) (Aromaticity is lost). (D) (Aromaticity bord) remains Both the resonatic structures are equivalent . So the acidity of compound (1) is highest