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

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

Rajasthan PMTRajasthan PMT 2011

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}}\, $

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