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Question 64 of 83

Q.Explain only reaction mechanism for alkaline hydrolysis of tert-butylbromide.

Maharashtra MsbshseMaharashtra HSC (MSBSHSE) Board 2018Subjective· 2mImportance★★★★★
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A tertiary halide ionises first (rate-determining step, stabilised carbocation), then the nucleophile attacks the planar cation in a fast second step.

tert-Butyl bromide, (CH3)3C−Br(CH_3)_3C-Br, being a tertiary alkyl halide, undergoes alkaline hydrolysis by the SN1S_N1 (substitution, nucleophilic, unimolecular) mechanism, in two steps:

Step 1 (slow, rate-determining): the polarised C–Br bond breaks heterolytically without any assistance from the incoming nucleophile, generating a planar tertiary carbocation (stabilised by hyperconjugation and the electron-donating inductive effect of the three methyl groups) and a bromide ion:

(CH3)3C−Br→slow(CH3)3C++Br−(CH_3)_3C-Br \xrightarrow{\text{slow}} (CH_3)_3C^+ + Br^-

Step 2 (fast): the hydroxide ion, a strong nucleophile, rapidly attacks the planar, electrophilic carbocation (from either face, since it's planar/sp² at the reacting carbon), giving the alcohol product:

(CH3)3C++OH−→fast(CH3)3C−OH(CH_3)_3C^+ + OH^- \xrightarrow{\text{fast}} (CH_3)_3C-OH

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