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Preparation of Haloalkanes from Alcohol

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Question

Compare rate of reaction with ${A g}^{⨁} {N O}_{3}^{⊖}$ or rate $S_{N^{1}}$ reaction:

i > ii > iii

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ii > iii > i

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ii > i > iii

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i > iii > ii

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Solution

The correct option is A i > ii > iii
The Rate of reaction with $A g N O_{3}$ is (i) > (ii) > (iii).

Rate is directly proportional to
Weak nucleophile with low concentration is required
Better leaving group is required for the reaction
Formation of carbocation should be stable
Alkyl halide is sterically hindered
Polar protic solvent with high dielectric constant is required

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