question_answer

Ozonolysis of a hydrocarbon gives one mole of acetone and one mole of formaldehyde. The hydrocarbon is

A)  propene

B)  2-methylpropene

C)  2-methyl-2-butene

D)  2-methyl-1-butene

Correct Answer: B

Solution :

As formaldehyde has one carbon atom and acetone has three carbon atoms, thus, the alkene must have four carbon atoms, \[i.e.,\] \[2-\]methyl propene. \[\underset{(reductive\,\,cleavage)}{\mathop{\xrightarrow[-ZnO]{Zn/{{H}_{2}}O}}}\,\underset{acetone}{\mathop{C{{H}_{3}}-\overset{\begin{smallmatrix}  C{{H}_{3}} \\  || \end{smallmatrix}}{\mathop{C}}\,=O}}\,+\underset{formaldehyde}{\mathop{O=\overset{\begin{smallmatrix}  H \\  || \end{smallmatrix}}{\mathop{C}}\,-H}}\,\]