JEE Main & Advanced Chemistry Nitrogen Containing Compounds Question Bank Self Evaluation Test - Amines

  • question_answer
    Which of the following amines will react with cyclohexanone to give enamine?

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

    B)

    C)            

    D) All of these

    Correct Answer: D

    Solution :

    [d] Carbonyl compounds containing at least one \[\alpha \]-hydrogen atom react with a Secondary amine to give enamine  \[\underset{\text{Primary}\,\,\text{amines}\,\,\text{also}\,\,\text{form}\,\,\text{enamines}}{\mathop{>CH-\overset{|}{\mathop{C}}\,=O+HN<_{R}^{R}\xrightarrow[-{{H}_{2}}O]{{}}C=\overset{|}{\mathop{C}}\,-N<_{R}^{R}}}\,\] \[\underset{\text{enamine}}{\mathop{>CH-\overset{|}{\mathop{C}}\,=O+{{H}_{2}}N-R}}\,\xrightarrow{{}}>C=\overset{|}{\mathop{C}}\,-N<_{R}^{H}\rightleftharpoons \,\,>\underset{\text{imine}}{\mathop{CH-\overset{|}{\mathop{C}}\,=N-R}}\,\] In second case enamme - amine tautomerism is possible and equilibrium lies completely on the imine side.


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