Which of the following compounds is obtained when t-butyl bromide is treated with alcoholic ammonia? - Chemistry

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MCQ

Which of the following compounds is obtained when t-butyl bromide is treated with alcoholic ammonia?

Options

  • \[\begin{array}{cc}
    \ce{CH3}\phantom{....}\\
    |\phantom{.......}\\
    \ce{CH3 - C - CH2 - NH2}\\
    |\phantom{.......}\\
    \ce{Br}\phantom{......}
    \end{array}\]

  • \[\begin{array}{cc}
    \ce{CH3 - C = CH2}\\
    |\phantom{.}\\
    \phantom{..}\ce{CH3}
    \end{array}\]

  • \[\begin{array}{cc}
    \phantom{...}\ce{CH3}\\
    |\\
    \ce{CH3 - C - CH3}\\
    |\\
    \phantom{...}\ce{NH2}
    \end{array}\]

  • \[\begin{array}{cc}
    \phantom{...}\ce{CH3}\\
    |\\
    \ce{CH3 -  C - CH3}\\
    |\\
    \phantom{.....}\ce{NHBr}
    \end{array}\]

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Solution

\[\begin{array}{cc}
\ce{CH3 - C = CH2}\\
|\phantom{.}\\
\phantom{..}\ce{CH3}
\end{array}\]

Explanation:

In presence of alcoholic ammonia, t-butyl bromide undergoes elimination (no substitution) to give isobutylene.

\[\begin{array}{cc}
\phantom{.}\ce{CH3}\phantom{.......................}\ce{CH3}\phantom{........}\\
\phantom{}|\phantom{...........................}|\phantom{..........}\\
\ce{CH3 - C - CH3 + \underset{{(alc.)}}{NH3} -> \underset{isobutylene}{CH3 - C = CH2} + NH4Br}\\
|\phantom{......................................}\\
\ce{\underset{{t-butyl bromide}}{Br}}\phantom{.................................}
\end{array}\]

Concept: Classification of Halogen Derivatives
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