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Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes

Identify the correct order of reactivity for the following compounds towards the S _ N 1 reaction: (I) (II) (III)

Options

  1. A(II) > (III) > (I)
  2. B(I) > (III) > (II)
  3. C(III) > (II) > (I)
  4. D(I) > (II) > (III)

Correct answer

C. (III) > (II) > (I)

Step-by-step solution

The reactivity of alkyl halides towards the S _ N 1 reaction depends on the stability of the intermediate carbocation formed. The given compounds form the following carbocations upon the loss of a chloride ion: (I) Cyclopropyl cation (II) Cyclobutyl cation (III) Cyclopentyl cation The positively charged carbon atom in a carbocation is sp^2 hybridized, which has an ideal bond angle of 120^ . The stability of these cyclic carbocations is determined by the angle strain, which is the difference between the ideal bond a

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