Punjab Medical Punjab - MET Solved Paper-2006

  • question_answer
    Which of the following compounds will be most reactive towards nucleophilic addition reaction?

    A) \[C{{H}_{3}}COC{{H}_{2}}C{{H}_{2}}C{{H}_{2}}C{{H}_{3}}\]

    B) \[C{{H}_{3}}C{{H}_{2}}OC{{H}_{2}}C{{H}_{2}}C{{H}_{3}}\]

    C) \[C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}CHO\]

    D) \[C{{H}_{3}}-C{{H}_{2}}-CO-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,H-C{{H}_{3}}\]

    Correct Answer: C

    Solution :

    The case with which a nucleophile attacks the carbonyl groups depends upon the electron-deficiency, i. e., magnitude of the positive charge on the carbonyl carbon. Since an alkyl groups has electron-donating inductive effect (+7 effect), therefore, greater the number of alkyl groups attached to the carbonyl group greater is the electron-density on the carbonyl carbon and hence, lower is its reactivity towards  nucleophilic  addition reactions.


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