Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Aldehydes, Ketones and Carboxylic Acids

Question:

A carbonyl compound A(C4H8O), which undergoes haloform reaction gives compound B on reduction. B on heating with sulphuric acid gives a compound C which forms a mono-ozonide D. D on hydrolysis in present of zinc dust gives only acetaldehyde E. 

Identify the compound C? 

Options:

Butane 

Butanoic acid

2-Butene 

None of the above 

Correct Answer:

2-Butene 

Explanation:

The correct answer is option 3. 2-Butene .

Since carbonyl compound A(C4H8O) undergoes haloform reaction, it must contain the group CH3CO. Therefore, it is a ketone and must be biutan-2-one.

Since ketone A, i.e., butan-2-one gives compound B on reduction, therefore B must be 2-butanol.

Since B, i.e., 2-Butanol on heating with H2SO4 gives compound C which forms a mono-ozonide, therefore compound C must be an alkene.

Since alkene C forms a mono-ozonide D which on hydrolysis in presence of zinc dust (i.e., reductive ozonolysis) gives only acetaldehyde E, therefore, C must be symmetrical alkene , i.e., 2-Butene.

All  the reactions involved are: