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Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes

Identify the correct order of reactivity of the following compounds towards the S _ N 1 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 reactivity of alkyl halides towards the S _ N 1 reaction depends on the stability of the carbocation intermediate formed after the departure of the leaving group (chloride ion). The carbocations formed from the given compounds are: (I) Cyclopropylmethyl cation (II) Tricyclopropylmethyl cation (III) Dicyclopropylmethyl cation The cyclopropylmethyl cation is exceptionally stable due to the delocalization of the -electrons of the bent bonds (banana bonds) of the cyclopropyl ring into the vacant p-orbital of the ad

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