Question

Convert the following :

Read the following passage and answer the questions that follow : A class of organic molecules which contain a carbon atom connected to an oxygen atom by a double bond is called Aldehydes and Ketones. It is called as carbonyl group. Aldehydes are prepared by the oxidation of alcohols. Formaldehyde is sold in an aqueous solution called formalin. Propanone, a simplest ketone is commercially prepared by fermenting corn or by oxidation of propan-2-ol. Carboxylic acids also have carbonyl carbon. They can be prepared by the oxidation of alcohols and aldehydes. Formic acid was first isolated by the distillation of red ants. It is partially responsible for the pain and irritation of ant and wasp stings. Aldehydes undergo many nucleophilic addition reactions. They can be reduced to primary alcohols. The aldehydes with α-hydrogen undergo aldol condensation and the aldehydes without α-hydrogen undergo Cannizzaro reaction. Ketones are highly reactive, although less so than aldehydes. Ketones are obtained by oxidation of secondary alcohols. Ketones possessing α-hydrogens also undergo aldol condensation. Carboxylic acids occur widely in nature and are used in the production of plastics, esters, etc. Aspirin is prepared from acetic acid. Similar to aldehydes and ketones, carboxylic acids can be halogenated at the α-carbon by reacting with a halogen in presence of phosphorus.

Compound A undergoes Rosenmund reduction to give compound B with molecular formula C₇H₆O. Compound B does not give Fehling's test but reacts with conc. NaOH to give C and D. Identify A, B, C and D and write all the reactions involved. Write one chemical test to distinguish between compound B and propanone.

Compound A with molecular formula (C₂H₆O) on oxidation by PCC gives compound B, which on treatment with dilute alkali forms compound C which is a β-hydroxy aldehyde. B on oxidation by potassium permanganate forms C. Identify A, B, C and D and write all the chemical equations involved.