NEET AIPMT SOLVED PAPER 1998

  • question_answer
                    Which one of the following esters cannot undergo Claisen self-condensation?                  

    A)                 \[C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}COO{{C}_{2}}{{H}_{5}}\]                                        

    B)                 \[{{C}_{6}}{{H}_{5}}COO{{C}_{2}}{{H}_{5}}\]

    C)                 \[{{C}_{6}}{{H}_{5}}C{{H}_{2}}COO{{C}_{2}}{{H}_{5}}\]                                                  

    D)                 \[{{C}_{6}}{{H}_{11}}C{{H}_{2}}COO{{C}_{2}}{{H}_{5}}\]

    Correct Answer: B

    Solution :

                    It is due to presence of \[\alpha \]-hydrogen atom in ester                 \[C{{H}_{3}}-C{{H}_{2}}-C{{H}_{2}}-C{{H}_{2}}-\]                                 \[{{C}_{6}}{{H}_{5}}COO{{C}_{2}}{{H}_{5}}+{{C}_{6}}{{H}_{5}}COO{{C}_{2}}{{H}_{5}}\]                 \[\to \] No reaction because for Claisen condensation an ester with two \[\alpha \]-hydrogens atoms are required                                                                                                   \[{{C}_{6}}{{H}_{11}}\,C{{H}_{2}}CO\underset{\begin{smallmatrix}  | \\  {{C}_{6}}{{H}_{11}} \end{smallmatrix}}{\mathop{C}}\,H-COO{{C}_{2}}{{H}_{5}}+{{C}_{2}}{{H}_{5}}OH\]                


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