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?

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One frequently used method for preparing methyl esters is by reaction
of carboxylic acids with diazomethane, CH,N2.
HO.
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?
Transcribed Image Text:One frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH,N2. HO. 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?
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