A) 2-methyl-2-butene
B) 3-methyl-1-butene
C) Cyclopentane
D) 2-methyl-1-butene
Correct Answer: A
Solution :
During ozonolysis,\[C=C\]bond breaks and each double bonded carbon atom is oxidized. \[\underset{2-methyl-2butene}{\mathop{C{{H}_{3}}CH-\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}\,-C{{H}_{3}}}}\,\xrightarrow{Zn/{{H}_{2}}O}\underset{ethanal}{\mathop{C{{H}_{3}}-CHO}}\,\] \[\underset{acetone}{\mathop{+{{(C{{H}_{3}})}_{2}}C}}\,=O\] \[\underset{3-methyl-1-butene}{\mathop{C{{H}_{3}}\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{CH}}\,-CH=C{{H}_{2}}}}\,\xrightarrow[Zn/{{H}_{2}}O]{{{O}_{3}}}\] \[\underset{2-methyl\,propanal}{\mathop{{{H}_{3}}C-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{CH}}\,-CHO}}\,+\underset{\begin{align} & \\ & \\ & \\ & methanal \\ \end{align}}{\mathop{HCHO}}\,\] Cyclopentane does not react with ozone. \[\underset{2-methyl-1-butene}{\mathop{C{{H}_{3}}-C{{H}_{2}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,=C{{H}_{2}}}}\,\xrightarrow[Zn/{{H}_{2}}O]{{{O}_{3}}}\] \[\underset{butene-2-one}{\mathop{C{{H}_{3}}C{{H}_{2}}-\underset{\begin{smallmatrix} | \\ {{H}_{3}}C \end{smallmatrix}}{\mathop{C}}\,=O+}}\,\underset{\begin{align} & \\ & \\ & \\ & mehanal \\ \end{align}}{\mathop{HCHO}}\,\] Hence, only 2-methyl-2-butene on ozonolysis gives acetone.
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