Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
Identify the correct decreasing order of reactivity of the given compounds towards the S _ N 2 reaction: (i) (ii) (iii)
Options
- A(iii) > (i) > (ii)
- B(i) > (iii) > (ii)
- C(i) > (ii) > (iii)
- D(ii) > (iii) > (i)
Correct answer
D. (ii) > (iii) > (i)
Step-by-step solution
The rate of an S _ N 2 reaction is inversely proportional to the steric hindrance around the electrophilic carbon atom. A bulkier group near the reaction center blocks the backside attack of the incoming nucleophile, thereby decreasing the reactivity. Let us analyze the steric hindrance in the given compounds: 1. In compound (i), 1-chloro-2,2,6,6-tetramethylcyclohexane, the carbon bonded to the chlorine atom is flanked by two quaternary -carbons (C2 and C6). The four bulky methyl groups at the -positions severely b