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24. Enolate Chemistry: Reactions at the Alpha-Carbon

Haloform Reaction

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Haloform Reaction

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Haloform Reaction

Haloform Reaction

Johnny Betancourt

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Multiple Choice

Provide the major product for the following reaction.

Textbook Question

In the presence of excess base and excess halogen, a methyl ketone is converted to a carboxylate ion. The reaction is known as the haloform reaction because one of the products is haloform (chloroform, bromoform, or iodoform). Before spectroscopy became a routine analytical tool, the haloform reaction served as a test for methyl ketones: the formation of iodoform, a bright yellow compound, signaled that a methyl ketone was present. Why do only methyl ketones form a haloform?

Textbook Question

Predict the products of the following reactions. (b) 1-phenylethanol + excess I2 in base

Textbook Question

Which compounds will give positive iodoform tests? (a) 1-phenylethanol (b) pentan-2-one (c) pentan-2-ol (d) pentan-3-one (e) acetone (f) isopropyl alcohol

Textbook Question

Predict the products of the following reactions.

(a) cyclopentyl methyl ketone + excess Cl₂ + excess NaOH

(b) 1-cyclopentylethanol + excess I₂ + excess NaOH

(c) propiophenone + excess Br₂ + excess NaOH

Textbook Question

Show how you would accomplish the following conversions

in good yields. You may use any necessary reagents.

(c) <IMAGE of reaction>

Textbook Question

Propose a mechanism for the reaction of cyclohexyl methyl ketone with excess bromine in the presence of sodium hydroxide.

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