Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Identify the correct order of acidic strength for the following compounds: (i) (ii) (iii)
Options
- A(i) > (ii) > (iii)
- B(ii) > (iii) > (i)
- C(iii) > (i) > (ii)
- D(i) > (iii) > (ii)
Correct answer
A. (i) > (ii) > (iii)
Step-by-step solution
The acidic strength of carboxylic acids is directly proportional to the stability of their conjugate base. Electron-withdrawing groups (EWGs) increase acidity via the -I effect by stabilizing the carboxylate ion, while electron-donating groups (EDGs) decrease acidity via the +I effect. In compound (i), the -NC group is a very strong EWG. Its powerful -I effect strongly stabilizes the conjugate base, making it the most acidic among the given compounds. In compound (ii), the -Cl group is also an EWG, but its -I effec