Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Identify the correct decreasing order of acidic strength for the following compounds: (i) (ii) (iii)
Options
- A(i) > (ii) > (iii)
- B(ii) > (i) > (iii)
- C(i) > (iii) > (ii)
- D(iii) > (ii) > (i)
Correct answer
A. (i) > (ii) > (iii)
Step-by-step solution
The given compounds are: (i) 2,4-dinitrobenzoic acid (ii) 3,4-dinitrobenzoic acid (iii) 3,5-dinitrobenzoic acid The acidic strength of substituted benzoic acids is enhanced by the presence of electron withdrawing groups. The NO₂ group exerts strong -I and -M effects. Compound (i) possesses an NO₂ group at the ortho position. Due to the ortho effect, it is significantly more acidic than the other isomers. The additional NO₂ group at the para position further increases its acidic strength. Hence, (i) is the most acid