why curtius rxn?

[dental17]

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Hello!

A problem in the KBB asked to convert RCOOH to RNH2. The solution was to transform the carboxylic acid to an acid chloride using SOCl2, followed by the Curtius rearrangement to get RNH2.

RCOOH + SOCl2 --> RCOCl + NaN3--> RNCO + H2O/-CO2--> RNH2

I am wondering why the Schmidt reaction wasn't used.

RCOOH ---> HN/H2SO4---> RNH2

 

[herkulease]

chances are they are using the "longer" method as the schimdt reaction is not one of the named reactions you expecting you to know.

But the "longer" method is one that they expect you to know and you should now the intermediates if you will of that synthesis. You might just be asked to use just some of those reagents in other synthesis.

If you know both you're good.

 

[dental17]

Thanks, herkulease! 🙂