Question

An unsaturated hydrocarbon $\mathrm{X}$ on ozonolysis gives $\mathrm{A}$. Compound $\mathrm{A}$ when warmed with ammoniacal silver nitrate forms a bright silver mirror along the sides of the test tube. The unsaturated hydrocarbon $\mathrm{X}$ is:

• A.
• B.
• C.
• D.

Answer 1

The correct option is C

Explanation for the correct option:

C) Ammoniacal silver nitrate reacts only with aldehyde group not with ketone group.

So among the options, only the following compound produces an aldehyde group on ozonolysis.

In the above diagram, the formed compound is not aldehyde but formic acid which contains aldehyde($\mathrm{H}-\mathrm{C}=\mathrm{O}$) as well as carboxylic group($\mathrm{O}=\mathrm{C}-\mathrm{OH}$) which behave as a reducing agent. Hence it will give positive Tollen's test i.e, formation of silver mirror takes place.

Explanation for the incorrect options:

A)

B)

D)

Both the product produced are ketones which do not react with ammoniacal silver nitrate.

Hence option C is correct.