Fundamentals of Organic ChemistryChemistryCarboxylic Acid Derivatives
Arrange the following groups in decreasing order of their leaving group ability: (I) (II) (III) - OMe (IV)
Options
- A(I) > (II) > (IV) > (III)
- B(IV) > (I) > (II) > (III)
- C(IV) > (I) > (III) > (II)
- D(II) > (I) > (IV) > (III)
Correct answer
B. (IV) > (I) > (II) > (III)
Step-by-step solution
The leaving group ability of an anion is inversely proportional to its basicity. A weaker base is a more stable anion and thus a better leaving group. The basicity of an anion can be compared by looking at the acidic strength of its conjugate acid. A stronger acid will have a weaker, more stable conjugate base. The conjugate acids for the given leaving groups are: (I) p -Toluenesulfonic acid ( p - CH ₃ C ₆ H ₄ SO ₃ H ) (II) Acetic acid ( CH ₃ COOH ) (III) Methanol ( CH ₃ OH ) (IV) Trifluoromethanesulfonic acid ( CF