Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Aldehydes, Ketones and Carboxylic Acids

Question:

Answer the question on the basis of passage given below:
Aldehydes are generally more reactive than ketones in nucleophilic addition reactions due to steric and electronic reasons. Sterically, the presence of two relatively large substituents in ketones hinders the approach of nucleophile to carbonyl carbon more than aldehydes having only one such substituent Electronically aldehydes are more reactive than ketones because two alkyl groups reduce the elctrophilicity of the carbonyl more effectively than in former.

Formaldehyde on reaction with benzaldehyde in basic medium gets converted to:

Options:

Methanol

Formic acid

o/p-hydroxymethylbenzaldehyde

o/p-hydroxymethyl benzoic acid

Correct Answer:

Formic acid

Explanation:

The correct answer is option 2. Formic acid.

The given conditions refers to Cannizzaro reaction. The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction that involves the base-induced disproportionation of an aldehyde lacking a hydrogen atom in the alpha position.

Mechanism:

The reaction involves a nucleophilic acyl substitution on an aldehyde, with the leaving group concurrently attacking another aldehyde in the second step. First, hydroxide attacks a carbonyl. The resulting tetrahedral intermediate then collapses, re-forming the carbonyl and transferring hydride to attack another carbonyl. In the final step of the reaction, the acid and alkoxide ions formed exchange a proton. In the presence of a very high concentration of base, the aldehyde first forms a doubly charged anion from which a hydride ion is transferred to the second molecule of aldehyde to form carboxylate and alkoxide ions. Subsequently, the alkoxide ion acquires a proton from the solvent.