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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.

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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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Most popular questions from this chapter

Question: What cyclic product is formed when each 1,5-dicarbonyl compound is treated with aqueous OH?

Question: Draw the products formed in each crossed aldol reaction.

a.

b.

Question: Devise a synthesis of each compound from CH3CH2CH2CO2Et, benzene, and alcohols having ≤ 2 C's. You may also use any required organic or inorganic reagents.

Question: Devise a synthesis of 2-methylcyclopentanone from cyclohexene. You may also use any required reagents

Question: Acid-catalyzed dehydration of β-hydroxy carbonyl compounds occurs by the mechanism discussed in Section 9.8. With this in mind, draw a stepwise mechanism for the following reaction.
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