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Chapter 22: Q15P (page 1163)

Propose a mechanism for the acid-catalyzed bromination of pentan-3-one.

Short Answer

Expert verified

The halogenation of ketones is catalyzed by acid. The ketone is dissolved in acetic acid, which serves as both the solvent and the acid catalyst.

Acidic halogenation can selectively replace just one hydrogen or more than one, depending on the amount of the halogen added.

Step by step solution

01

Acid-Catalyzed Alpha Halogenation

The halogenation of ketones is catalyzed by acid. The ketone is dissolved in acetic acid, which serves as both the solvent and the acid catalyst.

Acidic halogenation can selectively replace just one hydrogen or more than one, depending on the amount of the halogen added.

02

Mechanism of Acid-catalyzed bromination of pentan-3-one

Under acid catalysis, the ketone( pentan-3-one) is in equilibrium with its enol form. The enol acts as a weak nucleophile, attacking bromine to give a resonance-stabilized intermediate. Loss of a proton (deprotonation) results in the formation of the product 2-bromopentan-3-one.

Formation of 2-bromopentan-3-one

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Most popular questions from this chapter

Predict the products of self-condensation of the following esters.

(a) methyl propanoate +

(b) ethyl phenylacetate + NaOCH2CH3

(c)

(d)

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

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.

Which compounds will give positive iodoform tests?

  1. 1-phenyl ethanol
  2. pentan-2-ol
  3. pentan-2-one
  4. pentan-3-one
  5. acetone
  6. isopropyl alcohol

Predict the products of the following reactions.

  1. cyclopentyl methyl ketone + excess CI2 + excess NaOH
  2. 1-cyclopentylethanol + excess I2 + excess NaOH
  3. propiophenone + excess Br2 + excess NaOH
See all solutions

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