Q.(a) Complete the reaction: HCHO + C6H5CHO --50% NaOH--> [2 marks]
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Start your 14-day free trial to unlock the full solution →(a) Formaldehyde and benzaldehyde, both lacking alpha-H, undergo a CROSSED Cannizzaro reaction in 50% NaOH - formaldehyde is always the one oxidized (it is the better hydride donor), while benzaldehyde is reduced. (b) Clemmensen reduction converts C=O directly to CH2 using zinc amalgam and concentrated HCl. (c) Ethanoic acid is converted to glycolic acid via alpha-halogenation (HVZ reaction) followed by hydrolysis.
(a) HCHO + C6H5CHO --(50% NaOH)-->
Both formaldehyde and benzaldehyde have NO alpha-hydrogen, so neither can undergo an aldol reaction; instead, in the presence of concentrated (50%) NaOH, they undergo a CROSSED CANNIZZARO REACTION - an intermolecular disproportionation where one molecule is oxidized (to the carboxylate) and the other is reduced (to the alcohol). Formaldehyde, being a much better hydride donor (less hindered, more electrophilic carbonyl), is ALWAYS the one that gets oxidized in a crossed Cannizzaro with an aromatic aldehyde, while the aromatic aldehyde is reduced:
HCHO + C6H5CHO + NaOH --> HCOONa (sodium formate) + C6H5CH2OH (benzyl alcohol)
(b) Clemmensen reduction:
This is a method for reducing the carbonyl group (C=O) of an aldehyde or ketone directly and completely to a methylene group (-CH2-), using zinc amalgam [Zn(Hg)] and concentrated hydrochloric acid:
C=O --(Zn(Hg), conc. HCl)--> >CH2
It is particularly useful for reducing carbonyl compounds that are STABLE to acidic conditions (for base-sensitive substrates, the analogous Wolff-Kishner reduction, using NH2NH2/KOH, is used instead).
(c) Ethanoic acid -> 2-Hydroxyethanoic acid (glycolic acid): …
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