A) \[\text{C}{{\text{H}}_{\text{3}}}\text{-}\overset{\begin{smallmatrix} \text{C}{{\text{H}}_{\text{3}}} \\ \text{ }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{CH}}}\,\text{-}\underset{\begin{smallmatrix} \text{ }\!\!|\!\!\text{ } \\ \text{C}{{\text{H}}_{\text{3}}} \end{smallmatrix}}{\mathop{\text{CH}}}\,\text{-}\underset{\begin{smallmatrix} \text{ }\!\!|\!\!\text{ } \\ \text{C}{{\text{H}}_{\text{3}}} \end{smallmatrix}}{\mathop{\text{CH}}}\,\text{-}\overset{\begin{smallmatrix} \text{C}{{\text{H}}_{\text{3}}} \\ \text{ }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{CH}}}\,\text{-C}{{\text{H}}_{\text{3}}}\]
B) \[\text{C}{{\text{H}}_{\text{3}}}\text{C}{{\text{H}}_{\text{2}}}\text{-}\underset{\begin{smallmatrix} \text{ }\!\!|\!\!\text{ } \\ \text{C}{{\text{H}}_{\text{3}}} \end{smallmatrix}}{\overset{\begin{smallmatrix} \text{C}{{\text{H}}_{\text{3}}} \\ \text{ }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}}\,\text{---}\underset{\begin{smallmatrix} \text{ }\!\!|\!\!\text{ } \\ \text{C}{{\text{H}}_{\text{3}}} \end{smallmatrix}}{\overset{\begin{smallmatrix} \text{C}{{\text{H}}_{\text{3}}} \\ \text{ }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}}\,\text{-C}{{\text{H}}_{\text{2}}}\text{C}{{\text{H}}_{\text{3}}}\]
C) \[\text{C}{{\text{H}}_{\text{3}}}\text{-}\underset{\begin{smallmatrix} \text{ }\!\!|\!\!\text{ } \\ \text{OH} \end{smallmatrix}}{\mathop{\text{CH}}}\,\text{-}\underset{\begin{smallmatrix} \text{ }\!\!|\!\!\text{ } \\ \text{C}{{\text{H}}_{\text{3}}} \end{smallmatrix}}{\mathop{\text{CH}}}\,\text{-C}{{\text{H}}_{\text{3}}}\]
D) \[\text{C}{{\text{H}}_{\text{3}}}\text{-C}{{\text{H}}_{\text{2}}}\text{-}\underset{\begin{smallmatrix} \text{ }\!\!|\!\!\text{ } \\ \text{C}{{\text{H}}_{\text{3}}} \end{smallmatrix}}{\overset{\begin{smallmatrix} \text{C}{{\text{H}}_{\text{3}}} \\ \text{ }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}}\,\text{-B}{{\text{H}}_{\text{2}}}\]
Correct Answer: A
Solution :
\[C{{H}_{3}}-CH=\underset{\begin{smallmatrix} \text{ }\!\!|\!\!\text{ } \\ \text{C}{{\text{H}}_{\text{3}}} \end{smallmatrix}}{\mathop{\text{C}}}\,-C{{H}_{3}}\xrightarrow[{}]{B{{H}_{3}}.THF}\] \[\text{C}{{\text{H}}_{\text{3}}}\text{-}\underset{\begin{smallmatrix} \text{ }\!\!|\!\!\text{ } \\ \text{C}{{\text{H}}_{\text{3}}} \end{smallmatrix}}{\mathop{\text{CH}}}\,\text{-}\underset{\begin{smallmatrix} \text{ }\!\!|\!\!\text{ } \\ \text{B}{{\text{H}}_{\text{3}}} \end{smallmatrix}}{\mathop{\text{CH}}}\,\text{-C}{{\text{H}}_{\text{3}}}\xrightarrow[{}]{{}}\] \[{{\text{(C}{{\text{H}}_{\text{3}}}\text{-}\underset{\begin{smallmatrix} \text{ }\!\!|\!\!\text{ } \\ \text{C}{{\text{H}}_{\text{3}}} \end{smallmatrix}}{\mathop{\text{CH}}}\,\text{-}\underset{\begin{smallmatrix} \text{ }\!\!|\!\!\text{ } \\ \text{C}{{\text{H}}_{\text{3}}} \end{smallmatrix}}{\mathop{\text{CH}}}\,\text{-)}}_{\text{3}}}\text{B}\xrightarrow[{}]{\text{AgN}{{\text{O}}_{\text{3}}}}\] \[\text{C}{{\text{H}}_{\text{3}}}\text{-}\underset{\begin{smallmatrix} \text{ }\!\!|\!\!\text{ } \\ \text{C}{{\text{H}}_{\text{3}}} \end{smallmatrix}}{\mathop{\text{CH}}}\,\text{-}\underset{\begin{smallmatrix} \text{ }\!\!|\!\!\text{ } \\ \text{C}{{\text{H}}_{\text{3}}} \end{smallmatrix}}{\mathop{\text{CH}}}\,\text{-}\underset{\begin{smallmatrix} \text{ }\!\!|\!\!\text{ } \\ \text{C}{{\text{H}}_{\text{3}}} \end{smallmatrix}}{\mathop{\text{CH}}}\,-\underset{\begin{smallmatrix} \text{ }\!\!|\!\!\text{ } \\ \text{C}{{\text{H}}_{\text{3}}} \end{smallmatrix}}{\mathop{\text{CH}}}\,-\text{C}{{\text{H}}_{\text{3}}}\]
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