MCQ
A compound $A$ with molecular formula $C_{10}H_{13}Cl$ gives a white precipitate on adding silver nitrate solution.  $A$ on reacting with alcoholic $KOH$ gives compound $B$ as the main product. $B$ on ozonolysis gives $C$ and $D.$ $C$ gives Cannizaro reaction but not aldol condensation. $D$ gives aldol condensation but not Cannizaro reaction. $A$ is
  • A
    $C_6H_5 - CH_2 - CH_2 - CH_2 - CH_2 - Cl$
  • B
    $\begin{array}{*{20}{c}}
    {{C_6}{H_5} - C{H_2} - C{H_2} - CH - C{H_3}}\\
    {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,\,\,\,\,\,}\\
    {\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,Cl}\,\,\,\,\,\,
    \end{array}$
  • $C_6H_5 -CH_2$   $ - \begin{array}{*{20}{c}}
      {} \\ 
      {} \\ 
      C \\ 
      | \\ 
      {Cl} 
    \end{array} < \begin{array}{*{20}{c}}
      {C{H_3}} \\ 
      {C{H_3}} 
    \end{array}$
  • D

Answer

Correct option: C.
$C_6H_5 -CH_2$   $ - \begin{array}{*{20}{c}}
  {} \\ 
  {} \\ 
  C \\ 
  | \\ 
  {Cl} 
\end{array} < \begin{array}{*{20}{c}}
  {C{H_3}} \\ 
  {C{H_3}} 
\end{array}$
c
Compound $A$ reacts with alc. $KOH$ to give compound $B$ which on further ozonolysis gives $C$ (does not contains $\alpha -H$ atom) and $D$ (contains $\alpha -H$ atom). This reaction sequence can be achieved by compound in option $(a)$ and $(c)$. Since compound $A$ gives white ppt. with $AgNO_3$ preferable option will be $(c)$ as tert alkyl reacts with $AgNO_3$ more quickly.

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