Question:hard

The compound that CANNOT be obtained from the aldol condensation reaction shown below, is

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To solve aldol condensation predicting problems: 1. Locate the active \(\alpha\)-hydrogens. Here, they reside exclusively on the single \(\text{-CH}_2-\) group of the ketone. 2. The condensation product must feature a double bond connected directly to that specific carbon. 3. Structures (1), (3), and (4) maintain this connectivity. Structure (2) fails to maintain an \(\alpha,\beta\)-unsaturated framework conjugated with the carbonyl.
Updated On: Jun 21, 2026
  • FigA
  • FigB
  • FigC
  • FigD
Show Solution

The Correct Option is B

Solution and Explanation

Step 1: Recall how aldol condensation works.
Aldol condensation needs an alpha-hydrogen so a base can make an enolate. That enolate then attacks the carbonyl of the partner, and after loss of water an alpha,beta-unsaturated product forms.
Step 2: Look at the two starting carbonyls.
Benzaldehyde (PhCHO) has no alpha-hydrogen, so it can only be the electrophile (the acceptor). The 2,2-dimethylcyclopentanone is the partner that must supply the enolate.
Step 3: Find the usable alpha-carbon.
In 2,2-dimethylcyclopentanone, one alpha-carbon next to the C=O is fully substituted by two methyls and has no hydrogen, so no enolate can form there. The other alpha-carbon does carry hydrogens.
Step 4: Decide which products are reachable.
Only the alpha-carbon that has hydrogens can condense with benzaldehyde to give a benzylidene product on that side of the ring. Any product showing the new double bond on the blocked, fully methylated side cannot form.
Step 5: Match the impossible structure.
The structure in option 2 (FigB) is the one that would require enolate formation at the carbon with no alpha-hydrogen, so it cannot be obtained from this aldol condensation.
Step 6: State the answer.
The compound that cannot be obtained is FigB.
\[ \boxed{\text{FigB cannot be obtained}} \]
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