MCQ
Consider the following reaction, $\begin{matrix}
   C{{H}_{3}}-CH-CH-C{{H}_{3}}+\overset{\centerdot }{\mathop{B}}\,r  \\
   |\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
   \,\,D\,\,\,\,\,\,\,\,\,C{{H}_{3}}\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
\end{matrix}$ $\to X + HBr$ Indentify the structure of major poroduct $X$
  • A
    $\begin{matrix}
       C{{H}_{3}}-CH-CH-\overset{\centerdot }{\mathop{C}}\,{{H}_{2}}  \\
       \,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
       \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,D\,\,\,\,\,\,\,\,\,\,\,\,C{{H}_{3}}\,\,\,\,\,\,\,\,\,\,\,\,  \\
    \end{matrix}$
  • $\begin{matrix}
       C{{H}_{3}}-CH-\overset{\centerdot }{\mathop{C}}\,-C{{H}_{3}}  \\
       \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
       \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,D\,\,\,\,\,\,\,\,\,\,\,\,C{{H}_{3}}\,\,\,\,\,\,\,\,\,\,\,\,  \\
    \end{matrix}$
  • C
    $\begin{matrix}
       C{{H}_{3}}-\overset{\centerdot }{\mathop{C}}\,-CH-C{{H}_{3}}  \\
       \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,\,\,\,|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
       \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,D\,\,\,\,C{{H}_{3}}\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
    \end{matrix}$
  • D
    $\begin{matrix}
       C{{H}_{3}}-\overset{\centerdot }{\mathop{C}}\,H-CH-C{{H}_{3}}  \\
       \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,\,\,  \\
       \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,C{{H}_{3}}  \\
    \end{matrix}$

Answer

Correct option: B.
$\begin{matrix}
   C{{H}_{3}}-CH-\overset{\centerdot }{\mathop{C}}\,-C{{H}_{3}}  \\
   \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,  \\
   \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,D\,\,\,\,\,\,\,\,\,\,\,\,C{{H}_{3}}\,\,\,\,\,\,\,\,\,\,\,\,  \\
\end{matrix}$
b
$\begin{matrix}
   C{{H}_{3}}-CH-CH-C{{H}_{3}}  \\
   |\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,  \\
   D\,\,\,\,\,\,\,\,\,C{{H}_{3}}  \\
\end{matrix}+\overset{\centerdot }{\mathop{Br}}\,$ $ \to $ $\underset{{{3}^{o}}\,free\,radical\,[more\,stable]}{\mathop{\begin{matrix}
   C{{H}_{3}}-CH-\overset{\centerdot }{\mathop{C}}\,-C{{H}_{3}}  \\
   \,\,|\,\,\,\,\,\,\,\,\,\,\,\,|\,\,  \\
   \,\,\,\,D\,\,\,\,\,\,C{{H}_{3}}  \\
\end{matrix}}}\,+HBr$

$C-H$ bond energy is less than $C-D$ bond energy

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