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Chapter 24: Q.32. (page 962)

Question: Draw the product formed when each dicarbonyl compound undergoes an intramolecular aldol reaction followed by dehydration.

Short Answer

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Answer

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01

Intra-molecular aldol reaction

This reaction produces a five or six-membered ring as the two carbonyl groups tend to make a C-C bond within the same compound.

02

Aldol product dehydration

Upon dehydration, the β-hydroxy carbonyl product of the aldol reaction forms an α,β-unsaturated aldehyde or ketone.

03

Product of the given reaction

a. Since the enolizable carbonyl group and the α-carbon is 5 carbon atoms apart, the ring formed is five-membered.


Product of a.


b. Since the enolizable carbonyl group and the α-carbon is 6 carbon atoms apart, the ring formed is six-membered.

Product of b.

c. Since the enolizable carbonyl group and the α-carbon is 6 carbon atoms apart, the ring formed is six-membered.

Product of c.

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