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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

  1. A(iii) > (i) > (ii)
  2. B(i) > (iii) > (ii)
  3. C(i) > (ii) > (iii)
  4. 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

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