Multiple Bond Formation Synthesis of Sodium Azide

Another synthesis of hydrazine involves the oxidation of urea, (NH2)2C=0, with sodium hypochlorite  

4 MULTIPLE BOND FORMATION SYNTHESIS OF SODIUM AZIDE 

The structure of the azide anion (N3 ) indicates that the NH2 and N2O nitrogens must somehow come together and the H and O atoms somehow stripped away. A reasonable working hypothesis is that the amide ion (NH2 ) acts as a nucleophile and attacks one of the N2O nitrogens. For NH2 attacking the terminal nitrogen of N2O, the following pathway 

The NH proton of the intermediate can then be picked up by a second NH2 , producing NH3, N3, and OH , as shown below  

Let us now consider a pathway where NH2 attacks the middle (i.e nonterminal) nitrogen of N2O. A couple of the first steps would then be as follows  

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A.4 MULTIPLE BOND FORMATION SYNTHESIS OF SODIUM AZIDE 135... 

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