1.

Discuss the mechanism ofhydrolysis of tert - butyl bromide.

Answer»

Solution :Tertiary alkyl halides, undergo `SN^(1)` reaction. `SN^(1)` MECHANISM follows FIRST order kinetics.
Example : Tertiary butyl bromide on hydrolysis with aqueous `NaOH` gives tertiary butyl alcohol.
`underset("(Tertairy butyl bromide)")(CH_(3)-overset(CH_(3))overset("|")underset(CH_(3))underset("|")"C "-Br+NaOH)rarr underset("(Tertiary butyl alcohol)")(CH_(3)-overset(CH_(3))overset("|")underset(CH_(3))underset("|")"C "-OH+NaBr)`
Mechanism :-
I STEP : (slow step)
Tertiary butyl bromide ionises slowly to give `Sp2` hybridised PLANAR tertiary butyl carbocation and bromide ion

II Step : (FAST step)
The nucleophile `OH^(-)` from aqueous `NaOH` attacks planar carbocation on either side to give tertiary butyl alcohol


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