Q25 / 68 · NEST (NISER) 2022 (Session 1) · Chemistry

The compound $\mathbf{X}$, shown below, does not react with aq. NaOH at $80^{\circ} \mathrm{C}$. The reason is that


Figure

  • A
    the two methyl groups offer steric hindrance to the incoming nucleophile.
  • B
    the $\mathrm{C}-\mathrm{Cl}$ bond is strong and does not dissociate under the reaction conditions.
  • C
    the +I effect of the methyl groups destabilizes the carbocation.
  • Correct answer
    D
    the cyclic structure prevents the formation of the carbocation.

Hence, the correct answer is option: 'D'.

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