Question

$t-$ butyl chloride preferably undergo hydrolysis by

• A. ${{S}_{N}}1$ mechanism
• B. ${{S}_{N}}2$ mechanism
• C. Any of (a) and (b)
• D. None of the above

Answer 1

Answer: (A)

${{S}_{N}}1$ mechanism

Answer 2

Tertiary halide preferentially undergo ${{S}_{N}}1$ substitution as they can give stable carbocation. $\underset{t-butyl\,\,chloride}{\mathop{{{H}_{3}}C-\underset{\begin{smallmatrix} | \\\ C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix} C{{H}_{3}} \\\ | \end{smallmatrix}}{\mathop{C}}}\,-Cl}}\,\xrightarrow[-Cl]{slow}\underset{\begin{smallmatrix} {{3}^{o}}carbocation \\\ (most\,\,stable) \end{smallmatrix}}{\mathop{{{({{H}_{3}}C)}_{3}}{{C}^{+}}}}\,\xrightarrow[fast]{+O{{H}^{-}}}$ $\underset{t-butyl\,\,alcohol}{\mathop{{{({{H}_{3}}C)}_{3}}COH}}\,$