Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
Identify the correct reactivity order for the S _ N 2 reaction among the following compounds: (i) (ii) (iii)
Options
- A(ii) > (iii) > (i)
- B(iii) > (i) > (ii)
- C(i) > (iii) > (ii)
- D(iii) > (ii) > (i)
Correct answer
D. (iii) > (ii) > (i)
Step-by-step solution
The reactivity of S _ N 2 reactions at the -position of heteroatoms depends on the polarizability of the heteroatom, steric factors, and ground-state stabilization. 1. Polarizability: Sulfur is larger and much more polarizable than oxygen. In the S _ N 2 transition state, the highly polarizable sulfur atom can better stabilize the partial charges and the electron-rich transition state compared to the less polarizable oxygen atom. This significantly lowers the activation energy for the reaction. 2. Anomeric Effect (