Single correct option
Hexane-2,5-dione, when heated with dilute aqueous NaOH, gives an intramolecular aldol condensation product. The product is
- A. 2-methylcyclopent-2-en-1-one
- B. cyclohex-2-en-1-one
- C. 3-methylcyclopent-2-en-1-one
- D. 3-methylcyclohex-2-en-1-one
Show answer and solution
Answer: (C) 3-methylcyclopent-2-en-1-one
In 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 -hydroxy ketone gives the conjugated enone with at C-2 and the double bond , the methyl on C-5: 3-methylcyclopent-2-en-1-one (five-membered rings are preferred over strained alternatives).
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