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Mustard gas (ClCH2CH2)2-S hydrolysed by ...

Mustard gas `(ClCH_2CH_2)_2-S` hydrolysed by water to `Cl(CH_2)_2 S(Ch_2)_2 OH` much faster than expected for a primary halide. Offer an explanation.

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Neighbouring group participation (i.e., anchimeric assistance) :

Since the rate of hydrolysis is much faster than that of `1^@ RX`, it follows that `E_(act)` of both steps is lower than `E_(act)` of one step `(SN^2)` mechanism for `1^@ RX`,
As the `EN` of `C` is same, we can not distinguish on the basic of inductive effect.
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CH-=C-CH_(2)-CH_(2)-CH_(2)OH

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Consider the following alkyl halides 1. (CH_3)_3 "CCH"_2Br 2. ClCH_2CH=CH_2 3. ClCH_2 CH_2 CH_3 4. BrCH_2CH_2CH_3 Arrange these alkyl halides in decreasing order of reactivity in Williamson reaction.

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