A ketone A which undergoes haloform reaction gives compound B on reduction. B on heating with sulphuric acid gives compound C, which forms mono-ozonide D. The compound D on hydrolysis in presence of zinc dust gives only acetaldehyde. Write the structures and IUPAC names of A, B and C. Write down the reactions involved.
Since the compound A gives a positive haloform test, this indicates the presence of one free methyl group attached to the carbonyl atom.
When this ketone is reduced, secondary alcohol is obtained which on further dehydration gives alkene as the product.
This alkene on ozonolysis produces only one ozonoid which indicate that only one double bond is present in the main hydrocarbon.
The compound D produces only acetaldehyde therefore 2 molecules of (CH3CH=) should be present in the compound C.
Therefore after understanding each and every step of the reaction, the compound A which satisfies all the above condition is But-2-one.
The complete reaction is as follows:
