1.

Predict the order of reacitivity of the following compounds in S_(N)1 and S_(N)2 reactions: (1) The four isomeric bromobutanes.

Answer»

Solution :The four isomericc bromobutances are as follows:
(a) `CH_(3)CH_(2)CH_(2)CH_(2)Br`, (b)
(c) `CH_(3)CH_(2)CH(Br)CH_(3)` and (d) `(CH_3)_(3)C-Br`.
In `S_(N)1` pathway, reactivity of the alkly halides increases as the stability of the corresponding carbocations increases. since stability of the order : `CH_(3)CH_(2)overset(color(red)(o+))(C)H_(2)(1^(@)) < (CH_(3))_(2)CHoverset(color(red)(o+))(C)H_(2)(1^(@))< CH_(3)CH_(2)overset(color(red)(o+))(C)H_(3)(2^(@)) < (CH_(3))_(3)overset(color(red)(o+))(C)(3^(@))`. [REMEMBER that electoron DONATING +I effect of `(CH_3)_(2)CH` - is greater than that of `CH_(3)CH_(2)CH_(2)`-], the reactivity increases in the order (a) < (b) < (c) < (d).


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