Reactions of amines with nitrous acid

[PremedSurvivor]

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Hello,

So the MCAT lists "Reactions of amines with nitrous acid" as an official topic, and yet neither TBR nor EM seem to mention it significantly.

What do we need to know about these reactions? Does this reaction have any biological application? Is there some sort of unique intermediate? And are they referring to aryl amines or just regular, aliphatic amines?

Edit: I did see it on page 72 of EM. I'm just wondering if that level of coverage of the reaction is sufficient for the purposes of the MCAT.

 

[gwjib04]

There's a medical connection to this reaction because secondary amines (with or without phenyl group) react with Nitrous Acid to make Nitrosamines (R₂N-N=O) which have been controversially called carcinogens.



Sodium nitrite was used for years as an anti-botulism food preservative until this came up. Later, it was found that some normal flora actually make nitrite in the gut.

Tertiary amines don't make nitrosamine.

From Loudon Organic Chemistry