Write SN1 mechanism for the reaction, hydrolysis of tertiary butyl halide
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The hydrolysis of tertiary butyl halide happens through the SN1 mechanism which follows first-order kinetics and undergoes through a carbocation mechanism. It occurs through the following steps. (CH3)3C--Br + OH- -------> (CH3)3C--OH + Br-
- (CH3)3C--Br ---------> (CH3)3C+ + Br- The polar C-Br bond undergoes bond breaking and forms tertiary carbocation and bromide ion. This carbocation is extra stable due to the presence of three +I methyl groups. This is the slowest and rate-determining step. Rate only depends on the concentration of alkyl halide. R = k[ alkyl halide].
- Attack of the nucleophile - (CH3)3C+ + OH- ---------> ( CH3)3--OH The OH- here acts as a nucleophile and attacks the positively charged carbocation, hence forming tertiary butyl alcohol. This is the last step.
- The polar protic solvent is used in this reaction to stabilize the carbocation.
- The product formed is a racemic mixture as it contains 50% of d-isomers and 50% of l-isomers. The nucleophilic attack on the positively charged sp2 hybridized carbocation can be from both the left or right side and both these directions have a 50% chance. So, a racemic mixture is formed.
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