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Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes

Identify the correct order of reactivity towards the S _ N 2 reaction for the following compounds: (i) (ii) (iii)

Options

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

Correct answer

A. (i) > (iii) > (ii)

Step-by-step solution

The rate of an S _ N 2 reaction is inversely proportional to the steric hindrance around the electrophilic carbon atom. In substituted cyclohexanes, the S _ N 2 reaction involves a backside attack by the nucleophile. This attack is significantly hindered by axial substituents at the 3- and 5-positions due to 1,3-diaxial steric interactions in the transition state. Let us analyze the steric hindrance in the given compounds: 1. Compound (i) is 1-chloro-4,4-dimethylcyclohexane. The methyl groups are located at the 4-p

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