JEE Advanced levelSingle correct optionDifficulty 3 of 3si245
The ketone shown is treated with excess IX2 in aqueous NaOH, warmed, and the mixture is then acidified; the organic acid formed is isolated. How many 1H NMR signals does that acid give (the acid O-H counts)? Chemically equivalent hydrogens give one signal; ignore coupling and axial/equatorial differences.
A2
B3
C4
D5
Answer: B
Butan-2-one (shown) contains CHX3C=O and undergoes the iodoform reaction: it gives CHIX3 and sodium propanoate; acidification gives propanoic acid, CHX3CHX2COOH, with CHX3, CHX2 and COOH, 3 signals.