Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
Identify the correct order of reactivity for the S _ N 2 reaction of the following compounds: (i) (ii) (iii)
Options
- A(i) > (iii) > (ii)
- B(ii) > (iii) > (i)
- C(iii) > (i) > (ii)
- D(i) > (ii) > (iii)
Correct answer
A. (i) > (iii) > (ii)
Step-by-step solution
The given compounds are derivatives of benzyl chloride undergoing an S _ N 2 reaction. In an S _ N 2 reaction, the rate depends on the electrophilicity of the carbon atom undergoing substitution and the stability of the transition state. The transition state in an S _ N 2 reaction has a partial negative charge on the central carbon atom. Electron-withdrawing groups (EWG) such as - NO ₂ exert -I and -R effects. They withdraw electron density from the benzene ring, which increases the electrophilicity of the benzylic