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Which compound in each of the following ...

Which compound in each of the following pairs will react faster in `SN_(2)` reaction with - OH? i. `CH_(3)Br` or `CH_(3) I` ii. `(CH_(3))_3 C Cl` or `CH_(3) Cl`

A

`CH_(3)Br, (CH_(3))_(3)C Cl, CH_(2) = CHBr`

B

`CH_(3)Br, (CH_(3))_(3) C Cl, CH_(2) =CH CH_(2)Br`

C

`CH_(3)I, CH_(3)Cl, CH_(3)-CH_(2)Br`

D

`CH_(3)I, CH_(3)Cl, CH_(2) = CHCH_(3)Br`

Text Solution

Verified by Experts

The correct Answer is:
D
`CH_(3)I` as `I^(-)` is a weaker base and a good leaving group, hence more reactive. `CH_3Cl` will react faster as the approach ofnucleophile to the substitution centre is easier in case of primary halides as opposed to tertiary halides due to steric hindrance. `CH_(2) = CHCH_(2)Br` will be less reactive as vinylic halides are unreactive towards `S_N2` reactions. This is because the planar geometry of the alkene does not allow back-side attack, and the electron-rich nature of the alkenedoes not attract nucleophiles.
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