A compound (X) containing C,H and O is unreactive towards sodium. It also does not react with Schiff's reagent. On refluxing with an excess of hydroiodic acid, (X) yields only one organic product (Y). On hydrolysis, (Y) yields a new compound (Z) which can be converted into (Y) by reaction with red phosphorus and iodine. The compound (Z) on oxidation with potassium permanganate gives a carboxylic acid. The equivalent weight of the acid is 60.

What happens when compound (X) on treatment with excess of Cl₂ in presence of light?

perchlorodiethyl ether

The correct answer is option 3. perchlorodiethyl ether

Given,

A compound \(X\) containing \(C\), \(H\) and \(O\) is not reactive towards sodium, so, it cannot be an acid or an alcohol. The compound \(X\) also does not react with \(Br_2\) and Schiff's base. So, it cannot be an aldehyde or a ketone.

On refluxing with an excess of hydroiodic acid, (\X\) yields only one organic product (Y), so it is a symmetrical ether.

The compound (Z) on oxidation with potassium permanganate gives a carboxylic acid and the equivalent weight of the acid is 60. Hence it can be ethanoic acid (atomic weight = 60), which is produced from the compound \(Z\) on reaction with \(KMnO_4\). So the compound \(Z\) is ethanol. \(Z\) reacts with \(I_2/P_4(red)\) to give the compound \(Y\) whic is ethyl iodidde. 

From these facts we can identify the compound \(X\) as diethyl ether.

Since the compound \(X\) is Dimethyl ether, which when reacts with \(Cl_2\) in the presence of sunlight  we get: