One frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH,N2. OCH3 + CH2N2 + N2 Methyl benzoate (100%) Benzoic acid Diazomethane The reaction occurs in two steps: (1) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a car- boxylate ion; and (2) reaction of the carboxylate ion with CH3N2+. (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2?

One frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH,N2. OCH3 + CH2N2 + N2 Methyl benzoate (100%) Benzoic acid Diazomethane The reaction occurs in two steps: (1) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a car- boxylate ion; and (2) reaction of the carboxylate ion with CH3N2+. (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2?

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter23: Carbonyl Condensation Reactions

Section23.SE: Something Extra

Problem 45MP

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