JEE Main & Advanced Chemistry GOC Question Bank Critical Thinking

  • question_answer Among the following compounds which can be dehydrated very easily is [AIEEE 2004]

    A) \[C{{H}_{3}}-C{{H}_{2}}-\underset{OH\ \ \ \ \ \ }{\overset{C{{H}_{3}}\ \ \ \ }{\mathop{\underset{|}{\overset{|}{\mathop{C}}}\,-C{{H}_{2}}}}}\,-C{{H}_{3}}\]

    B) \[C{{H}_{3}}-C{{H}_{2}}-C{{H}_{2}}-\overset{OH}{\mathop{\overset{|}{\mathop{C}}\,H}}\,-C{{H}_{3}}\]

    C) \[C{{H}_{3}}-C{{H}_{2}}-C{{H}_{2}}-C{{H}_{2}}-C{{H}_{2}}-OH\]

    D) \[C{{H}_{3}}-C{{H}_{2}}-\underset{C{{H}_{3}}\ }{\mathop{\underset{|}{\mathop{C}}\,H-}}\,C{{H}_{2}}-C{{H}_{2}}-OH\]

    Correct Answer: A

    Solution :

    \[C{{H}_{3}}-C{{H}_{2}}-\underset{OH\ \ \ \ \ \ \ }{\overset{C{{H}_{3}}\ \ \ \ \ }{\mathop{\underset{|}{\overset{|}{\mathop{C}}}\,-C{{H}_{2}}}}}\,-C{{H}_{3}}\xrightarrow{{{H}^{+}}}\]\[C{{H}_{3}}-C{{H}_{2}}-\overset{C{{H}_{3}}\ \ \ \ \,}{\mathop{\underset{\oplus }{\overset{|}{\mathop{C}}}\,-C{{H}_{2}}}}\,-C{{H}_{3}}\] The more stable carbocation is generated thus more easily it will be dehydrated.


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