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a) Write S_(N)1 mechanism for the hydrolysis of 2-Bromo-2-methyl propane. Why are S_(N)1 reactions generally carried in polar protic solvents? |
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Answer» Solution :`SN^(1)` mechanism FOLLOWS first order kinetics `underset("2 - Bromo -2 methyl propane")(CH_(3)-overset(CH_(3))overset("|")underset(CH_(3))underset("|")"C "-Br+NAOH)rarr underset("2 - metylpropan -2- OL")(CH_(3)-overset(CH_(3))overset("|")underset(CH_(3))underset("|")"C "-OH+NaBr)` 2-Bromo-2 methyl propane on hydrolysis with aqueous `NaOH` gives 2-metylpropan 2- o1 Mechanism `SN^(1)` mechanism involves two steps I Step (Slow step) Tertiary butyl bromide ionises slowly to GIVEN `SP^(2)` hybridised planar 2-methylpropane. cation  II Step (Slow step) The nucleophile `OH^(-)` from aqueous NaOH attacks planar carbocation on either side to GIVE (tertiary butyl alcohol) 2-Metylpropane cation  `3^(@)` Butyl alcohol obtained is a racemic mixture. Protic solvents solvate halide ion and provide energy so generally carried in polar protic solvents. |
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