Acid hydrolysis of symmetrical β-diketone to identical carboxylic acids

Steps:

• Identify compounds susceptible to acid hydrolysis: ethers and β-diketones can react, but check product empirical formulas.
• For B (CH3COCH2COCH3), recognize as symmetrical 1,3-diketone with empirical formula C5H8O2.
• Hydrolysis cleaves central C-C bond: CH3COCH2COCH3 + H2O → 2 CH3COOH.
• Both products have identical empirical formula C2H4O2, matching the condition.

Why B is correct:

• Symmetrical β-diketones undergo acid-catalyzed hydrolysis (reverse of Claisen condensation) to yield two molecules of the same carboxylic acid, here acetic acid (C2H4O2).

Why the others are wrong:

• A: α-Hydroxy ketone lacks cleavable bond for hydrolysis; no products with matching empirical formulas.
• C: Ether cleavage by HCl gives C2H5Cl (C2H5Cl) and C2H5OH (C2H6O), different empirical formulas.
• D: Diether hydrolysis yields mixed alcohols and halides like C2H5OH (C2H6O) and HOCH2CH2OH (C2H6O2), not identical.

Final answer: B