Chemistry - Aromatic Hydrocarbon Question with Solution | TestHub

Based on the formula of hydrocarbon${\mathrm{C}}_{\mathrm{n}}{\mathrm{H}}_{2\mathrm{n}-4}$the degree of unsaturation is 3. So, there is two case:

(I) 3 double bonds

(II) 1 double bond and 1 triple bond

Second case can be easily rejected because products of ozonolysis are aldehyde or ketone rather than carboxylic acid.

So the alkene would be:

$(\mathrm{C}{\mathrm{H}}_3{)}_2\mathrm{C}\mathrm{H}\mathrm{C}{\mathrm{H}}_2\mathrm{C}\mathrm{H}=\mathrm{C}\mathrm{H}\mathrm{C}{\mathrm{H}}_2\mathrm{C}{\mathrm{H}}_2\mathrm{C}\mathrm{H}=\mathrm{C}\mathrm{H}\mathrm{C}{\mathrm{H}}_2\mathrm{C}{\mathrm{H}}_2\mathrm{C}\mathrm{H}=\mathrm{C}{\left(\mathrm{C}{\mathrm{H}}_3\right)}_2$

Which on ozonolysis will give products as:

${\left(\mathrm{C}{\mathrm{H}}_3\right)}_2\mathrm{C}\mathrm{H}\mathrm{C}{\mathrm{H}}_2\mathrm{C}\mathrm{H}=\mathrm{C}\mathrm{H}\mathrm{C}{\mathrm{H}}_2\mathrm{C}{\mathrm{H}}_2\mathrm{C}\mathrm{H}=\mathrm{C}\mathrm{H}\mathrm{C}{\mathrm{H}}_2\mathrm{C}{\mathrm{H}}_2\mathrm{C}\mathrm{H}=\mathrm{C}{\left(\mathrm{C}{\mathrm{H}}_3\right)}_2$

$\stackrel{\mathrm{O}\mathrm{z}\mathrm{o}\mathrm{n}\mathrm{o}\mathrm{l}\mathrm{y}\mathrm{s}\mathrm{i}\mathrm{s}}{\to } (\mathrm{C}{\mathrm{H}}_3{)}_2\mathrm{C}\mathrm{H}\mathrm{C}{\mathrm{H}}_2\mathrm{C}\mathrm{H}\mathrm{O}+2\mathrm{O}\mathrm{H}\mathrm{C}\mathrm{C}{\mathrm{H}}_2\mathrm{C}{\mathrm{H}}_2\mathrm{C}\mathrm{H}\mathrm{O}+\mathrm{C}{\mathrm{H}}_3\mathrm{C}\mathrm{O}\mathrm{C}{\mathrm{H}}_3$

The formula of alkene is${\mathrm{C}}_{16}{\mathrm{H}}_{28}$

So the value of ‘x’ is 16.