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Q.a) How does formaldehyde reacts with concentrated alkali on heating? Name this reaction.

(3)
b) Identify the reagent "X" and "Y" used in the following conversion.
(2)
C6H5CH3+X→CS2C6H5CH(OCrOHCl2)2→+YC6H5CHO\text{C}_6\text{H}_5\text{CH}_3 + X \xrightarrow{\text{CS}_2} \text{C}_6\text{H}_5\text{CH(OCrOHCl}_2)_2 \xrightarrow{+Y} \text{C}_6\text{H}_5\text{CHO}
Karnataka PUCKarnataka II PUC Board 2022Subjective· 5mImportance★★★★★
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Formaldehyde undergoes the Cannizzaro reaction with conc. alkali to give methanol + sodium formate; in the toluene → benzaldehyde (Étard) conversion X is chromyl chloride CrO2Cl2\text{CrO}_2\text{Cl}_2 and Y is acid hydrolysis (H3O+\text{H}_3\text{O}^+).

a) Formaldehyde + concentrated alkali (Cannizzaro reaction)

Aldehydes that have no α-hydrogen atom (such as formaldehyde, HCHO) cannot undergo aldol condensation. Instead, when heated with a concentrated alkali, two molecules undergo a self oxidation–reduction (disproportionation) — one molecule is reduced to an alcohol while the other is oxidised to the salt of a carboxylic acid. This is the Cannizzaro reaction:

2 HCHO+NaOH→ΔCH3OH+HCOONa2\,\text{HCHO} + \text{NaOH} \xrightarrow{\Delta} \text{CH}_3\text{OH} + \text{HCOONa}

(one HCHO → methanol; the other HCHO → sodium formate).

b) Reagents X and Y (toluene → benzaldehyde, Étard reaction)

Toluene is oxidised to benzaldehyde by chromyl chloride in carbon disulphide (CS2\text{CS}_2). This forms a brown chromium complex (the intermediate shown, C6H5CH(OCrOHCl2)2\text{C}_6\text{H}_5\text{CH(OCrOHCl}_2)_2), which on acidic hydrolysis gives benzaldehyde: …

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