VMMC VMMC Medical Solved Paper-2014

  • question_answer
    How many chiral compounds are possible on monochlorination of 2-methyl butane?

    A) 2                                             

    B) 4

    C) 6                                             

    D) 8

    Correct Answer: B

    Solution :

    \[C{{H}_{3}}-C{{H}_{2}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{CH}}\,-C{{H}_{3}}\xrightarrow[{}]{C{{l}_{2}}}\] \[C{{H}_{3}}-C{{H}_{2}}-\underset{(I)}{\mathop{\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,-}}\,C{{H}_{2}}Cl\] \[\underset{(II)}{\mathop{+C{{H}_{3}}-C{{H}_{2}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix}  Cl \\  | \end{smallmatrix}}{\mathop{C}}}\,-C{{H}_{3}}}}\,\] \[\underset{(III)}{\mathop{C{{H}_{3}}-\underset{*}{\mathop{\overset{\begin{smallmatrix}  Cl \\  | \end{smallmatrix}}{\mathop{C}}\,}}\,H-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{CH}}\,-C{{H}_{3}}}}\,\] \[\underset{(IV)}{\mathop{+\underset{\begin{smallmatrix}  | \\  Cl \end{smallmatrix}}{\mathop{C{{H}_{2}}}}\,-C{{H}_{2}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{CH}}\,-C{{H}_{3}}}}\,\] I and III have chirality*. Thus, in all four (including enantiomers) optical isomers are obtained.


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