PrepRung

JEE Main 2017 · Chemistry · Carbonyl Compounds, Carboxylic Acids and Amines · medium

Hexane-2,5-dione, when heated with dilute aqueous NaOH, gives an intramolecular aldol condensation product. The product is

Single correct option

Hexane-2,5-dione, when heated with dilute aqueous NaOH, gives an intramolecular aldol condensation product. The product is
  1. A. 2-methylcyclopent-2-en-1-one
  2. B. cyclohex-2-en-1-one
  3. C. 3-methylcyclopent-2-en-1-one
  4. D. 3-methylcyclohex-2-en-1-one
Show answer and solution

Answer: (C) 3-methylcyclopent-2-en-1-one

In CH3CO−CH2CH2−COCH3\mathrm{CH_3CO{-}CH_2CH_2{-}COCH_3} the enolate carbon of one methyl (C-1) can attack the carbonyl carbon C-5: ring includes C-1 to C-5, i.e. a five-membered ring. Attack of C-3 on C-5 would give a strained 3-membered ring. Dehydration of the β\beta-hydroxy ketone gives the conjugated enone with C=O\mathrm{C=O} at C-2 and the double bond C1=C5\mathrm{C1=C5}, the methyl on C-5: 3-methylcyclopent-2-en-1-one (five-membered rings are preferred over strained alternatives).
Report a mistake

Original question written in the JEE Main 2017 pattern and checked twice for the correct answer. Not an official question paper. How we write and check questions · Corrections policy · Report a mistake