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Chapter 24: Q.35. (page 962)

Question: What dicarbonyl compound is needed to prepare each compound by an intramolecular aldol reaction?

Short Answer

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Answer

Step by step solution

01

Detect the α and β carbons

The αandβ carbon bond is cleaved to open the ring.

02

Addition to the α and β-carbons

Upon cleavage, the α-carbon is added with a hydrogen atom. However, the β-carbon is converted into a carbonyl group(C=O) , and the tetravalency of the carbon is satisfied with the hydrogen atom.

03

Product of the given reaction

a. The starting materials of the product are detected hereunder.

Starting materials of a.

b. The starting materials of the product are detected hereunder.

Starting materials of b.


c. The starting materials of the product are detected hereunder.

Starting materials of c.

d. The starting materials of the product are detected hereunder.

Starting materials of d.

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Most popular questions from this chapter

Question: Draw the products of each reaction.

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

a.

b.

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.
  1. Question:β -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 β-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 β-vetivone.) (b) Draw a stepwise mechanism for the aldol reaction, which forms the six-membered ring.

Question:Coumarin, a naturally occurring compound isolated from lavender, sweet clover, and tonka bean, is made in the laboratory fromo-hydroxybenzaldehyde by the reaction depicted below. Draw a stepwise mechanism for this reaction. Coumarin derivatives are useful syntheticanticoagulants.
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