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Question
Identify the compound that will react with Hinsberg’s reagent to give a solid which dissolves in alkali.
Options
\[\begin{array}{cc}
\phantom{....}\ce{CH2}\phantom{.......}\phantom{}\\
\phantom{.}/\phantom{....}\backslash\phantom{....}\\
\phantom{}\ce{CH3}\phantom{......}\ce{\overset{\bullet\bullet}{N}H2}\phantom{..}
\end{array}\]\[\begin{array}{cc}
\phantom{..}\ce{CH2}\phantom{.......}\ce{CH2}\phantom{}\\
\phantom{.......}/\phantom{....}\backslash\phantom{.....}/\phantom{}\phantom{....}\backslash\phantom{.....}\\
\phantom{..}\ce{CH3}\phantom{........}\ce{\overset{\bullet\bullet}{N}}\phantom{........}\ce{CH3}\phantom{}\\
\phantom{..}|\\
\phantom{...}\ce{CH3}
\end{array}\]\[\begin{array}{cc}
\phantom{....}\ce{CH2}\phantom{.......}\phantom{}\\
\phantom{.}/\phantom{....}\backslash\phantom{....}\\
\phantom{}\ce{CH3}\phantom{......}\ce{\overset{\bullet\bullet}{N}O2}\phantom{..}
\end{array}\]\[\begin{array}{cc}
\phantom{........}\ce{CH2}\phantom{.......}\ce{CH3}\phantom{}\\
\phantom{.......}/\phantom{....}\backslash\phantom{.....}/\phantom{....}\\
\phantom{}\ce{CH3}\phantom{......}\ce{\overset{\bullet\bullet}{N}H}\phantom{..}
\end{array}\]
Solution
\[\begin{array}{cc}
\phantom{....}\ce{CH2}\phantom{.......}\phantom{}\\
\phantom{.}/\phantom{....}\backslash\phantom{....}\\
\phantom{}\ce{CH3}\phantom{......}\ce{\overset{\bullet\bullet}{N}H2}\phantom{..}
\end{array}\]