Organic Chemistry : Help with Haloform Reactions

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #5 : Carbonyl Reactions

Which of the following best summarizes the haloform reaction?

Possible Answers:

The enolate of an ester attacks another ester

An alkyl halide reacts first with the phthalimide ion, then with

The enolate of a dicarbonyl compound attacks a beta carbon of an alkene

A carboxylic acid reacts first with then with water

A methyl ketone is treated with iodine and

Correct answer:

A methyl ketone is treated with iodine and


The haloform reaction requires a carbonyl with a terminal alpha carbon. A hydrogen gets abstracted, and the enolate is formed. A halogen attacks the alpha carbon, and the ketone is reformed. This occurs three more times until the carbon has bonds to three halogens. Then the carbon leaves, forming a carbanion, and the base attacks the carbonyl carbon. An ester is formed.

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