Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Arrange the following compounds in decreasing order of their reactivity towards NH ₃ : (I) (II) (III) CH ₃ COCl
Options
- A(III) > (I) > (II)
- B(I) > (III) > (II)
- C(I) > (II) > (III)
- D(II) > (III) > (I)
Correct answer
A. (III) > (I) > (II)
Step-by-step solution
The reaction of these compounds with NH ₃ is an example of nucleophilic acyl substitution. The reactivity of acid derivatives towards nucleophilic substitution depends on the leaving group ability. A weaker base is a better leaving group. The leaving groups for the given compounds are: (I) Acetic anhydride: Acetate ion ( CH ₃ COO ⁻ ) (II) Methyl acetate: Methoxide ion ( CH ₃ O ⁻ ) (III) Acetyl chloride: Chloride ion ( Cl ⁻ ) The order of basicity of these leaving groups is: Cl ⁻ Therefore, the order of leaving grou