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Chapter 22: Q18P (page 1166)

Propose a mechanism for the aldol condensation of cyclohexanone. Do you expect the equilibrium to favor the reactant or the product?

Short Answer

Expert verified

Cyclohexanone reacts with the hydroxide ion to form theenolate which is resonance stabilized. Then the enolate acts as a nucleophile and attack on another molecule of cyclohexanone. In the last step, protonation by water gives the aldol product, which is 1鈥�-hydroxybi(cyclohexan)-2-one.

Formation of 1鈥�-hydroxybi(cyclohexan)-2-one

Step by step solution

01

Aldol condensation of cyclohexanone

Cyclohexanone reacts with the hydroxide ion to form theenolate which is resonance stabilized. Then the enolate acts as a nucleophile and attack on another molecule of cyclohexanone. In the last step, protonation by water gives the aldol product, which is 1鈥�-hydroxybi(cyclohexan)-2-one.

Formation of 1鈥�-hydroxybi(cyclohexan)-2-one

02

Equilibrium in Aldol condensation

Equilibrium in Aldol condensation of ketone recommends forming reactants, not products. The product formed in the aldol condensation is very bulky; thus,there is asignificant hindrance on both carbons with new bonds; therefore, the aldol condensation of cyclohexanone favor reactants at the equilibrium.

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Most popular questions from this chapter

Show how octane-2,7-dione might cyclize to a cycloheptenone. Explain why ring closure to the cycloheptenone is not favored.

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

For each molecule shown below,

  1. Indicate the most acidic hydrogens.
  2. Draw the important resonance contributors of the anion that results from removal of the most acidic hydrogen.

Propose a mechanism for the acid-catalyzed reaction of cyclohexanone with pyrrolidine.

When propionaldehyde is warmed with sodium hydroxide, one of the products is 2-methylpent-2-enal. Propose a mechanism for this reaction.
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