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Chemistry LibreTexts

Diazomethane

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Diazomethane, CH2N2, is a yellow, poisonous, potentially explosive compound, which is a gas at room temperature. The structure of diazomethane is explained using three resonance forms.

diazomethane1.png

In organic chemistry laboratory, diazomethane has two common uses.

1. Conversion of carboxylic acids to methyl esters

eg:

diazomethane2.png

mechanism:

diazomethane3.png

2. Conversion of alkenes to cyclopropanes

eg:

diazomethane4.png

mechanism:

diazomethane5.png

see also diazonium ion


This page titled Diazomethane is shared under a All Rights Reserved (used with permission) license and was authored, remixed, and/or curated by Gamini Gunawardena via source content that was edited to the style and standards of the LibreTexts platform.

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