Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Aldehydes, Ketones and Carboxylic Acids

Question:

Answer the question on basis of passage given below:

A ketone [A] which undergoes haloform reaction gives compound [B] on reduction. Compound [B] on heating with sulphuric acid gives compound [C] which forms monozonide [D]. The compound [D] on hydrolysis in the presence of zinc dust gives compound [E]. Compound [E] on oxidation gives \(C_2H_4O_2\)[F]

Compound [F] on treatment with chlorine, in presence of a small amount of red phosphorous gives:

 

Options:

\(CH_3CH_2-Cl\)

\(CH_3COCl\)

\(ClCH_2COOH\)

\(ClCH_2CH_2Cl\)

Correct Answer:

\(ClCH_2COOH\)

Explanation:

The correct answer is option 3. \(ClCH_2COOH\).

From the given data in the passage the various reactions and be depicted as:

The compound [F] is acetic acid.Acetic acid when reacts with with chlorine, in presence of a small amount of red phosphorous it undergoes Hell Volhard Zelinsky (HVZ) reaction.

The reaction conditions for the HVZ reaction are quite severe- involving reaction temperatures above 373 K and increased reaction time. The reaction usually requires less than one equivalent of phosphorous (or a trihalide of phosphorous). Some carboxylic acids and acid derivatives such as acyl halides or anhydrides can be halogenated in the absence of a catalyst.