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Which aldehyde would NOT undergo aldol condensation but WOULD undergo Cannizzaro?
A$CH_3CHO$ (acetaldehyde)
B$CH_3CH_2CHO$ (propanal)
C$(CH_3)_2CHCHO$ (isobutyraldehyde)
D$(CH_3)_3CCHO$ (pivaldehyde)
Answer & Solution
Correct answer: D. $(CH_3)_3CCHO$ (pivaldehyde)
Pivaldehyde has no $\alpha$-H (the $\alpha$-C is quaternary, bonded to three methyls), so aldol is impossible. Cannizzaro, which requires the *absence* of $\alpha$-H, is the available pathway. The other three all have $\alpha$-H and undergo aldol.
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