RAJASTHAN ­ PET Rajasthan PET Solved Paper-2006

  • question_answer
    When 3, 3-dimethyl-2-butanol is heated with \[{{H}_{2}}S{{O}_{4}}\]then the major product is

    A)  3, 3-dimethyl-l-butene

    B)  2, 3-dimethyl-2-butene

    C)  2, 3-dimethyl-l-butene

    D)  cis and trans isomers of product [b].

    Correct Answer: B

    Solution :

     On the dehydration of alcohol, a more stable alkene is formed as major product. According to Saytzeffs rule a more substituted alkene is more stable. \[C{{H}_{3}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}}\,-\underset{\begin{smallmatrix}  | \\  OH \end{smallmatrix}}{\mathop{CH}}\,-C{{H}_{3}}\xrightarrow[\Delta ]{Conc.{{H}_{2}}S{{O}_{4}}}\] \[\underset{2,3-dimethyl2-butene}{\mathop{C{{H}_{3}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,=\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}\,-C{{H}_{3}}}}\,\]


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