Seema Sinha Solutions for Chapter: Reduction and Oxidation Reactions of Organic Compounds, Exercise 2: DPP 2.2

An unknown hydrocarbon $\left(\mathrm{A}\right)$, with formula ${\mathrm{C}}_6{\mathrm{H}}_{12}$, react with $1$ molar equivalent of ${\mathrm{H}}_2$ over a palladium catalyst. Hydrocarbon $\mathrm{A}$ also react with ${\mathrm{OsO}}_4$ to give a diol $\left(\mathrm{B}\right)$. When oxidized with ${\mathrm{KMnO}}_4$ in acidic solution, '$\mathrm{A}$' gives two fragments. One fragment is propanoic acid and other fragment is a ketone $\left(\mathrm{C}\right)$. What are the structures of $\mathrm{A}, \mathrm{B}$ and $\mathrm{C}$ ?

The given reaction,

is an example of:

Product obtained in the above reaction is

The reaction,

An organic compound on reaction with ${\mathrm{O}}_3$ followed by $\mathrm{Zn}$ and ${\mathrm{H}}_2\mathrm{O}$ gives ${\mathrm{CH}}_3{\mathrm{COCH}}_2{\mathrm{CH}}_2{\mathrm{COCH}}_3$. The structures is/are:

Which of the following will give syn addition?

On oxidation, an unknown alkene ${\mathrm{C}}_8{\mathrm{H}}_{16}$ gives a mixture of propanoic acid and pentanoic acid. The unknown alkene can be:

Propan$-1-$ol and Propan$-2-$ol can be best distinguished by: