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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 α-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 β-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: 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.)

Question:What starting materials are needed to synthesize each compound by a crossed Claisen reaction?

Question: Devise a synthesis of each compound from cyclopentanone, benzene, and organic alcohols having ≤ 3 C's. You may also use any required organic or inorganic reagents.

Question: Zingerone, a spicy-sweet component of cooked ginger, can be converted to its protected TBDMS ether A, as we learned in Chapter 20. How can A be converted to gingerol, a compound present in fresh ginger, using a directed aldol reaction as a key step?

Question: Draw a stepwise mechanism for the conversion of heptane-2,6-dione to 3-methylcyclohex-2-enone with NaOEt, EtOH.
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