Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Alcohols, Phenols and Ethers

Question:

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 is the name of the Compound (Y)?

Options:

ethyl iodide

methyl iodide

propyl iodide

ethyl iodide and methyl iodide

Correct Answer:

ethyl iodide

Explanation:

The correct answer is option 1. ethyl iodide.

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.

Thus, the name of the compound \(Y\) is ethyl iodide.