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Chapter 22: Q32E (page 752)

Treatment of a cyclic ketone with diazomethane is a method for accomplishing a ring-expansion reaction.For example, treatment of cyclohexanone with diazomethane yields cycloheptanone. Propose a mechanism.

Short Answer

Expert verified

Ring expansion is the reaction to expanding existing rings and forming compounds.

Diazo methane helps in expanding the ring by one unit.

Step by step solution

01

Ring-expansion reaction

Ring expansion is the reaction to expanding existing rings and forming compounds.

Diazo methane helps in expanding the ring by one unit.

02

Mechanism

The mechanism for the given reaction involves the following steps:

The carbanion of the diazo methane reacts with the carbonyl carbon and forms the respective product.

Mechanism of the reaction

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Most popular questions from this chapter

Which of the following substances would undergo the haloform reaction?

(a)CH3COCH3 (b) Acetophenone (c) CH3CH2CHO

(d)CH3CO2H (e)CH3C≡N


The two optically beta-keto acids below were decarboxylated using the conditions typically used for the acetoacetate synthesis. Will the ketone products also be optically active? Provide the complete mechanism to explain your answer.

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(c) Ethyl acetate

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(f) Phenylacetone

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