Question

Major product formed in the following reaction:

\[\begin{array}{cc}
\ce{CH3}\phantom{.............}\\
|\phantom{...............}\\
\ce{CH3 - C - Br + NaOCH3 ->}\\
|\phantom{...............}\\
\ce{CH3}\phantom{.............}\\
\end{array}\]

Options

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

• \[\begin{array}{cc}
  \phantom{.}\ce{CH3}\\
  |\phantom{..}\\
  \ce{CH3 - C - OCH3}\\
  |\phantom{..}\\
  \phantom{.}\ce{CH3}\\
  \end{array}\]

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

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

Answer 1

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

Explanation:

\[\begin{array}{cc}
\ce{CH3}\phantom{...............................................}\\
|\phantom{.................................................}\\
\ce{CH3 - C - Br + NaOCH3 -> \ce{CH3 - C = CH2} + NaBr + CH3OH}\\
\phantom{............}|\\
\phantom{..............}\ce{CH3}\\
\end{array}\]

Tert-halide with a strong base favours the elimination reaction, not the substitution reaction.