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Chapter 24: Q.49. (page 962)

Question: What product (including stereochemistry) is formed in each of the following intramolecular reactions?

Short Answer

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Answer

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01

Intramolecular aldol reaction

In the presence of the reagents NaOEt and EtOH, the compound undergoes an intramolecular aldol reaction. In this reaction, the 伪-carbon of one of the carbonyl groups bonds with the carbonyl (C=O)carbon of another carbonyl group.

02

Dieckmannreaction

In this reaction, the ester group and the carbonyl group undergo a reaction to form a cyclic 尾-ketoesterin the presence of NaOEt and H3O+ reagents.

03

Explanation

a. The product including stereochemistry is shown hereunder.


b. The product including stereochemistry is shown here below:

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Most popular questions from this chapter

Question: Draw the aldol product formed from each pair of starting materials using OH,H2O.

Question: Devise a stepwise mechanism for the following reaction, a key step in the synthesis of the antibiotic abyssomicin C. Abyssomicin C was isolated from sediment collected from almost 1000 ft below the surface in the Sea of Japan. (Hint: The mechanism begins with a Dieckmann reaction.)
  1. Question:尾 -Vetivone is isolated from vetiver, a perennial grass that yields a variety of compounds usedin traditional eastern medicine, pest control, and fragrance. In one synthesis, ketone A is converted to 尾-vetivone by a two-step process: Michael reaction, followed by intramolecular 00a00000ldol reaction.000 (a) What Michael acceptor is needed for the conjugate addition? (See Problem23.61 for another method to form the bicyclic ring system of 尾-vetivone.) (b) Draw a stepwise mechanism for the aldol reaction, which forms the six-membered ring.

Question:When A is treated with aqueous 鈥揙H, the major product is compound B, which undergoes ester hydrolysis and decarboxylation to form C. Draw a stepwise mechanism for the conversion of A to B.

Question:What starting materials are needed to synthesize each compound using a Robinson annulation?
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