Q.Complete and rewrite the balanced chemical equations —
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Start your 14-day free trial to unlock the full solution →Chlorobenzene is cyanated to benzonitrile; isobutyraldehyde undergoes aldol addition (not condensation, since its alpha carbon becomes fully substituted); butanone forms its 2,4-DNP hydrazone.
a. Chlorobenzene + NaCN/CuCN, 473 K, pressure: this is a copper-catalysed cyanation (Rosenmund–von Braun-type) of the aryl chloride, replacing with :
b. Isobutyraldehyde + 50% KOH: isobutyraldehyde, , has exactly ONE -hydrogen (on the carbon bonded to ), so unlike formaldehyde/benzaldehyde (no -H, which undergo Cannizzaro's reaction), it undergoes aldol addition under concentrated base: base removes the single -H, the resulting carbanion/enolate attacks the carbonyl carbon of a second molecule, giving a -hydroxy aldehyde:
(3-hydroxy-2,2,4-trimethylpentanal). Notably, in this product the -carbon that reacted is now bonded to two methyl groups, the , and the new C–C bond — a fully-substituted (quaternary) carbon with no -hydrogen left, so the usual base-catalysed dehydration to an -unsaturated aldehyde cannot proceed further; the reaction stops at the aldol (addition) stage rather than going on to full 'condensation'.
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