Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Arrange the following compounds in decreasing order of their acidity: (i) CH ₃ CH ₂ OH (ii) CFH ₂ CO ₂ H (iii) CF ₂ HCO ₂ H (iv) CF ₃ COOH (v) CH ₃ CO ₂ H
Options
- A(iv) > (iii) > (ii) > (i) > (v)
- B(v) > (iii) > (iv) > (ii) > (i)
- C(v) > (ii) > (iii) > (iv) > (i)
- D(iv) > (iii) > (ii) > (v) > (i)
Correct answer
D. (iv) > (iii) > (ii) > (v) > (i)
Step-by-step solution
Carboxylic acids are significantly more acidic than alcohols because the carboxylate conjugate base is stabilized by resonance, whereas the alkoxide ion is not. Thus, CH ₃ CH ₂ OH (i) is the least acidic compound among the given options. Among the carboxylic acids, acidity increases with the presence of electron-withdrawing groups due to the -I (inductive) effect, which stabilizes the resulting carboxylate ion by dispersing the negative charge. Fluorine is highly electronegative and exerts a strong -I effect. As th