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JEE Chemistry 2025 Question with Solution

When

Organic compound structure shown for intramolecular aldol condensation, containing two carbonyl groups positioned to allow cyclization into a five-membered ring product.

undergoes intramolecular aldol condensation, the major product formed is:

  • A

    Option 1

  • B

    Option 2

  • C

    Option 3

  • D

    Option 4

Answer

Correct answer:C

Step-by-step solution

Standard Method

Given: The substrate undergoes intramolecular aldol condensation.

Find: The major cyclic product formed.

The solution explains that the given compound contains two carbonyl groups and forms an enolate at an α\alpha-position. In an intramolecular aldol reaction, the enolate attacks the other carbonyl group within the same molecule, so cyclization occurs.

A 55-membered ring is favored because intramolecular aldol condensations usually prefer formation of 55- or 66-membered rings, and here the 55-membered cyclic product is stated to be the major product.

After cyclization, the intermediate β\beta-hydroxy carbonyl compound undergoes dehydration to give an α,β\alpha,\beta-unsaturated carbonyl compound.

Therefore, the major product is the cyclic α,β\alpha,\beta-unsaturated carbonyl compound with a 55-membered ring. The solution identifies this as option C.

The correct option is C.

Mechanistic Explanation

Given: An intramolecular aldol condensation of a dicarbonyl compound.

Find: Which option represents the major product.

The extracted solution states the following sequence:

  1. Identify the enolizable hydrogen adjacent to a carbonyl group.
  2. Form the enolate ion.
  3. Carry out intramolecular nucleophilic attack on the other carbonyl carbon.
  4. Form a cyclic intermediate.
  5. Remove water by dehydration.

Because ring closure that gives a 55-membered ring is more stable, that pathway dominates over alternatives. The final product is therefore a conjugated cyclic enone/enal-type product formed after dehydration.

The source solution explicitly concludes: the correct answer is the third option, and the page marks The Correct Option is C.

Common mistakes

  • Choosing a product with the wrong ring size. Intramolecular aldol condensation usually favors 55- or 66-membered rings, so larger or strained alternatives are less likely. Check the carbon count during cyclization before selecting the product.

  • Forgetting the dehydration step. The aldol addition intermediate is a β\beta-hydroxy carbonyl compound, but the final major product of aldol condensation is typically the α,β\alpha,\beta-unsaturated carbonyl compound. Do not stop at the addition product.

  • Forming the enolate at an inappropriate position. Only α\alpha-hydrogens next to the carbonyl are enolizable in this mechanism. Identify the correct enolate-forming site first, then trace the intramolecular attack.

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