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]

Identify compound [A]

Options:

Butan-2-one

3-Methylpentan-2-one

Propane

Acetophenone

Correct Answer:

Butan-2-one

Explanation:

The correct answer is option 1.Butan-2-on.

The haloform reaction is a characteristic reaction of ketones with a methyl group adjacent to the carbonyl group. This reaction typically involves the oxidation of the methyl group to produce a carboxylate salt and iodoform \((CHI_3)\) as a by-product.

Here, the product of the reaction is the carboxylate salt (\( \text{R-COONa} \)) and iodoform (\( \text{CHI}_3 \)). The carboxylate salt formed from the haloform reaction can be reduced to an alcohol. For instance, sodium propionate (say) can be reduced to propanol.

When propanol is heated with sulfuric acid, it forms propene through dehydration. Propene reacts with ozone to form propene monozonide.

Hydrolysis of the propene monozonide in the presence of zinc dust yields acetaldehyde and formaldehyde. Finally, oxidation of acetaldehyde yields acetic acid. Acetic acid has the formula \(C_2H_4O_2\).