CET Karnataka Medical CET - Karnataka Medical Solved Paper-2014

  • question_answer
    The acid strength of active methylene group in (i) \[C{{H}_{3}}COC{{H}_{2}}COO{{C}_{2}}{{H}_{5}}\] (ii) \[C{{H}_{3}}COC{{H}_{2}}C{{H}_{3}}\] (iii) \[{{C}_{2}}{{H}_{5}}OOCC{{H}_{2}}COO{{C}_{2}}{{H}_{5}}\] decreases as

    A)  \[i>iii>ii\]      

    B)  \[i>ii>iii\]

    C) \[ii>i>iii\]     

    D)  \[iii>i>ii\]

    Correct Answer: C

    Solution :

    : In   active   methylene   compound (ii), methylene \[(-C{{H}_{2}})\] group exists in between two strong EWGs i.e. \[(-C{{H}_{3}}CO-)\], which increases the acidity. Esters (iii) are less acidic than ketones (i) because the enolate ion produced from an ester is less stable than that produced from a ketone. Hence, \[C{{H}_{3}}-\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,-\underset{(ii)}{\mathop{C{{H}_{2}}}}\,-\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,-C{{H}_{3}}\]     \[>C{{H}_{3}}-\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,-\underset{(i)}{\mathop{C{{H}_{2}}}}\,-\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,-O{{C}_{2}}{{H}_{5}}\] \[>{{C}_{2}}{{H}_{5}}O-\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,-\underset{(iii)}{\mathop{C{{H}_{2}}}}\,-\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,-O-{{C}_{2}}{{H}_{5}}\]


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