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Chapter 22: Q68P-c (page 1204)

Question:Show how you would use an aldol, Claisen, or another type of condensation to make each compound

c.

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01

 Aldol cyclisation

It is the nucleophilic acyl substitution reaction of the carbonyl group forming the enolate ion which leads to the cyclization with the carbonyl group in the molecule which leads to the formation of unsaturated ketone or aldehyde.

02

Formation of the product

As the hydrogen is protonated from the reacting species formation of enolate ion occurs which combines with its own carbonyl group followed by the removal of formation of unsaturated aldehyde or ketone occur as shown:

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Most popular questions from this chapter

Phenylacetone can form two different enols.

  1. Show the structures of these enols.
  2. Predict which enol will be present in the larger concentration at equilibrium.

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation.

(a) Although the following compound is a substituted acetone derivative, it cannot be made by the acetoacetic ester synthesis. Explain why (two reasons).

(b) The use of LDA to make enolate ions (Sections 22-2B and 22-3) has provided alternatives to the acetoacetic ester synthesis. Show how you might make the compound shown in part (a), beginning with 1,3-diphenylacetone.

(c) Enamine reactions (Section 22-4) occur under relatively mild conditions, and they often give excellent yields of compounds like the one shown in part (a). Show how you might use an enamine reaction for this synthesis, beginning with 1,3-diphenylacetone.

Show how you would use the malonic ester synthesis to make the following compounds

Show how the following ketones might be synthesized by using the acetoacetic ester synthesis.
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