Question

Under $ {{S}_{N}}1 $ conditions the hydrolysis o neo-pentyl bromide gives

• A. $ C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,=CH-C{{H}_{2}}OH $
• B. $ C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ OH \end{smallmatrix}}{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,-C{{H}_{2}}C{{H}_{3}} $
• C. $ C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,-C{{H}_{2}}OH $
• D. None of the above

Answer 1

Answer: (B)

$ \xrightarrow[{}]{1,2-Me\,shift}C{{H}_{3}}-\underset{\begin{smallmatrix} ({{3}^{o}})carbocation\, \\ (more\,stable) \end{smallmatrix}}{\mathop{\underset{\oplus }{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{-C{{H}_{2}}}}\,}}\, $ $ \xrightarrow[{}]{O{{H}^{-}}}C{{H}_{3}}-\underset{\begin{smallmatrix} ({{3}^{o}})carbocation\, \\ (more\,stable) \end{smallmatrix}}{\mathop{\underset{\oplus }{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{-C{{H}_{2}}}}\,}}\, $ $ \xrightarrow[{}]{O{{H}^{-}}}C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ OH \end{smallmatrix}}{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,-C{{H}_{2}}C{{H}_{3}} $