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JEE Main levelSingle correct optionDifficulty 2 of 3ro137

Hexane-1,6-diol, $HOCH X_{2} (CH X_{2}) X_{4} CH X_{2} OH$ , is oxidised separately with (i) excess PCC in $CH X_{2} Cl X_{2}$ and (ii) excess Jones reagent. The products are respectively

Ahexanedioic acid; hexanedial
B6-hydroxyhexanal; hexanedial
Chexanedial; hexane-1,6-dioic anhydride
Dhexanedial; hexanedioic acid

Answer: D

PCC in

CH X_{2} Cl X_{2}

stops at the aldehyde, converting both primary alcohol groups into

CHO

to give hexanedial. Aqueous acidic Jones reagent oxidises primary alcohols all the way to carboxylic acids, giving hexanedioic acid.

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