Up until this point, nitrogen was always that atom whose formal charge was a bit annoying to calculate. Yeah, we've seen nitrogen in a lot of acid-base reactions, and sure, nitrogen came back into the spotlight when we learned about amides. But now, nitrogen gets its five seconds of fame. In this series, gang, we do a deep dive on amines. We'll discuss their physical properties as well as how to produce them (in ways you already knew but also with new pathways). So buckle up: It's nitrogen time.
https://joechem.io/videos/86 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we get our feet wet with amines and start exploring this new functional group.
https://joechem.io/videos/87 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we look at different methods of producing amines, such as: 1.) alkylation 2.) reduction of a nitrile (-CN) 3.) reduction of azide (-N3)
https://joechem.io/videos/88 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link) In this video, we'll explore making Phthalimide, the key reagent used in the Gabriel Synthesis (see the Gabriel Synthesis video here https://joechem.io/videos/88). This will be an exercise in doing a double addition-elimination forming diamide reaction To be clear, this is NOT the Gabriel Synthesis, but I have seen teachers ask for this mechanism since it tests your addition elimination knowledge and can then feed into a Gabriel Synthesis question.
https://joechem.io/videos/195 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link) In this video, we'll explore the Gabriel Synthesis, using phthalimide to create primary amines. We'll step through the mechanism, and even take on a few complete the reaction/provide the reagent examples. This is how you'll (most likely) use this reaction in the course you're taking. If you want to see how to create phthalimide (and get more addition-elimination practice)
https://joechem.io/videos/89 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we take a look at Reductive Amination--its mechanism and how to predict products successfully. What's awesome is, if you put in the work back when we worked with imines (https://joechem.io/videos/34) this will be very familiar and a cakewalk for you.
https://joechem.io/videos/90 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we go through the mechanism behind the Mannich Reaction and get some practice with predicting the product. What's awesome is, if you put in the work back when we worked with imines (https://joechem.io/videos/34) and enols in the aldol condensation (https://joechem.io/videos/42) this will be very familiar and a lovely trip down memory lane.
https://joechem.io/videos/196 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link) In this video, we'll cover the Hofmann Elimination, the formation of the least substituted double bond (via E2), with an over alkylated amine as our leaving group. This is the same Hofmann Elimination that you may have been introduced to when you learned E2 for the first time, and in this video I explain why this reaction leads to the lesser substituted double bond. There is also another video with a specific, cyclic amine Hofmann Elimination example (made before this video), but this video is to be watched first. Hofmann Elimination with a Cyclic Amine - https://joechem.io/videos/91
https://joechem.io/videos/91 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we look at another Hofmann Elimination, this time with a cyclic amine. For an overview and full explanation of the Hofmann Elimination with Quaternary Amines, please see the following video below: Hofmann Eliminations (E2) with Quaternary Amines - https://joechem.io/videos/196