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\(\mathrm{CH}_{3}-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{Cl} \stackrel{\mathrm{aq}^{-1-1 \mathrm{OH}}}{\rightarrow} \mathrm{CH}_{3}-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{OH}\)
Which information below regarding this reaction is applicable?
(A) It follows \(S_{N} 2\) pathway, because it is a primary alkyl chloride.
(B) It follows \(\mathrm{S}_{\mathrm{N}} 1\) pathway, because the intermediate carbocation is resonance stabilized.
(C) \(\mathrm{S}_{\mathrm{N}} 1\) pathway is not followed, because the intermediate carbocation is destabilised by \(-1\) effect of oxygen
(D) A mixed \(S_{N} 1\) and \(S_{N} 2\) pathway is followed.

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Ans: (D)
 \(\mathrm{Cl}-\mathrm{O}-\mathrm{CH}_{2}\) Stabilised by resonance \(\Rightarrow \mathrm{S}_{\mathrm{N}} 1\)
\(\mathrm{S}_{\mathrm{N}} 2\) is also facilitated by \(\mathrm{OH}\) due to resonance stablization of transition state.
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