Skip to content
Question of 87

Q.Identify the structures of A,B and C.

(a) [a benzene ring drawn with a −COCH3-COCH_3 substituent and a −CH3-CH_3 substituent] →KMnO4, KOHA→dil. H2SO4B→HeatSOCl2C\xrightarrow{KMnO_4,\ KOH} A \xrightarrow{dil.\ H_2SO_4} B \xrightarrow[Heat]{SOCl_2} C OR
(b) CH3COCl→H2, Pd/BaSO4A→dil. NaOHB→H+/H2OCCH_3COCl \xrightarrow{H_2,\ Pd/BaSO_4} A \xrightarrow{dil.\ NaOH} B \xrightarrow{H^+/H_2O} C
Manipur CohsemCOHSEM Manipur Higher Secondary Board 2025Subjective· 3mImportance★★★★★
0% · 0/87 Questions
🔒 Locked · start free trial →

You're viewing a preview — the full solution, concept, methods & PYQ mapping are locked.

Start your 14-day free trial to unlock the full solution →

This question offers a choice between identifying A, B, C from a haloform-then-acid-chloride sequence on a disubstituted benzene (primary), or a straightforward reduction-hydrolysis-hydration sequence starting from acetyl chloride (the alternative). Both are answered below.

(Primary, a) — Starting material: a benzene ring bearing −COCH3-COCH_3 and −CH3-CH_3 substituents:

Step 1 (KMnO4KMnO_4, KOH): Hot alkaline KMnO4KMnO_4 is well known to oxidise a benzylic-type ring −CH3-CH_3 substituent all the way to −COOK-COOK (a carboxylate), while the separate ketone carbonyl (−COCH3-COCH_3) is comparatively resistant to further oxidation by KMnO4KMnO_4 under these conditions and survives unchanged. So A is the potassium salt of the ring-methyl-oxidised product: a keto-carboxylate, CH3CO−C6H4−COOKCH_3CO-C_6H_4-COOK.

Step 2 (dil. H2SO4H_2SO_4): Acidification converts the potassium carboxylate salt to the free carboxylic acid, B = CH3CO−C6H4−COOHCH_3CO-C_6H_4-COOH (a keto-acid).

Step 3 (SOCl2SOCl_2, heat): Thionyl chloride selectively converts the −COOH-COOH group to the corresponding acid chloride (the ketone carbonyl is unaffected by SOCl2SOCl_2), giving C = CH3CO−C6H4−COClCH_3CO-C_6H_4-COCl.

OR (b) — CH3COCl→A→B→CCH_3COCl \rightarrow A \rightarrow B \rightarrow C:

Step 1 (H2H_2, Pd/BaSO₄ — Rosenmund reduction): This mild, poisoned-catalyst hydrogenation reduces an acid chloride only as far as the aldehyde (not all the way to the alcohol), giving A = acetaldehyde, CH3CHOCH_3CHO:

CH3COCl→H2, Pd/BaSO4CH3CHO (A)CH_3COCl \xrightarrow{H_2,\ Pd/BaSO_4} CH_3CHO\ (A)

Step 2 (dil. NaOH): Base-catalysed aldol condensation of acetaldehyde with itself gives 3-hydroxybutanal, B:

…

Unlock everything free for 14 days

  • Full step-by-step solutions
  • Concept-first explanations
  • Methods, shortcuts & mistakes
  • PYQ mapping + timed mock tests

Full access for 14 days. No credit card required.