Exercise-3

A biologically active compound, Bombykol $\left({\mathrm{C}}_{16}{\mathrm{H}}_{30}\mathrm{O}\right)$ is obtained from a natural source. The structure of the compound is determined by the following reactions:

(a) On hydrogenation, Bombykol gives a compound $\mathrm{A},$ ${\mathrm{C}}_{16}{\mathrm{H}}_{34}\mathrm{O}$, which reacts with acetic anhydride to give an ester.

(b) Bombykol also reacts with acetic anhydride to give another ester, which on oxidative ozonolysis $\left({\mathrm{O}}_3/{\mathrm{H}}_2{\mathrm{O}}_2\right)$ gives a mixture of butanoic acid, oxalic acid and $10$-acetoxy decanoic acid.

Determine the number of double bonds in Bombykol. Write the structures of compound $\left(\mathrm{A}\right)$ and Bombykol. How many geometrical isomers are possible for Bombykol?

The decreasing order of the ratio of $\mathrm{HCN}$ addition to compounds $\mathrm{a}$ to $\mathrm{d}$ is:

$\left(\mathrm{a}\right) \mathrm{HCHO}$

$\left(\mathrm{b}\right) {\mathrm{CH}}_3{\mathrm{COCH}}_3$

$\left(\mathrm{c}\right) {\mathrm{PhCOCH}}_3$

$\left(\mathrm{d}\right) \mathrm{PhCOPh}$

Identify $\left(\mathrm{X}\right), \left(\mathrm{Y}\right)$ and $\left(\mathrm{Z}\right)$ in the following synthetic scheme and write their structures. Explain the formation of labelled formaldehyde $\left({\mathrm{H}}_2{\mathrm{C}}^{*}\mathrm{O}\right)$ as one of the products when compound $\left(\mathrm{Z}\right)$ is treated with $\mathrm{HBr}$ and subsequently ozonolysed. Mark the $\left({\mathrm{C}}^{*}\right)$ carbon in the entire scheme.

${\mathrm{BaC}}^{*}{\mathrm{O}}_3+{\mathrm{H}}_2{\mathrm{SO}}_4⟶\left(\mathrm{X}\right)$ (gas) [${\mathrm{C}}^{*}$denotes ${\mathrm{C}}^{14}$]

${\mathrm{CH}}_2=\mathrm{CH}·\mathrm{Br} \underset{\left(\mathrm{ii}\right)\mathrm{X}, \left(\mathrm{iii}\right) {\mathrm{H}}_3{\mathrm{O}}^{+}}{\overset{\left(\mathrm{i}\right) \mathrm{Mg}/\mathrm{Ether}}{\to }}\left(\mathrm{Y}\right)\stackrel{{\mathrm{LiAlH}}_4}{⟶}\left(\mathrm{Z}\right)$

In conversion of $2$ -butanone to propanoic acid which reagent is used?

Which one of the following undergoes reaction with $50\%$ sodium hydroxide solution to give the corresponding alcohol and acid?

In the Cannizzaro reaction given below,

 $2\mathrm{PhCHO} \stackrel{\stackrel{\mathrm{\Theta }}{\mathrm{O}}\mathrm{H}}{\to }{\mathrm{PhCH}}_2\mathrm{OH}+{\mathrm{PhCO}}_2^{\Theta }$, the slowest step is :

Trichloroacetaldehyde was subjected to the Cannizzaro's reaction by using $\mathrm{NaOH}$. The mixture of the products contain sodium trichloroacetate ion and another compound. The other compound is :

Identify the correct order of boiling points of the following compounds

$\begin{array}{ccc}{\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{OH},& {\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{CHO},& {\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{COOH}\\ \left(1\right)& \left(2\right)& \left(3\right)\end{array}$