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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

Show how an acetoacetic ester synthesis might be used to form a 未 -diketone such as heptane-2,6-dione.

Biochemists studying the structure of collagen (a fibrous protein in connective tissue) found cross-links containing 伪,尾unsaturated aldehydes between protein chains. Show the structures of the side chains that react to form these crosslinks, and propose a mechanism for their formation in a weakly acidic solution.

Predict the products of the following reactions.

a. Cyclopentanone +Br2 in acetic acid

b. 1phenylethanol + I2 excess

c.

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i)

Question:Show how you would use the Robinson annulation to synthesize the following compounds.

Show how you would accomplish the following conversions in good yields. You may use any necessary reagents.
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