Fresh off of our introduction to conjugation, we now understand the powerful stabilizing effect of having a network of consecutive atoms with unhybridized p orbitals parallel to one another. Well, in this series, we take it to the next level with the concept of aromaticity. Benzene is going to become our best friend in this series, and we'll see how, even though it is rock solid stable due to its aromaticity, to do chemical transformations with benzene and benzene derivatives. We'll learn a basic set of reactions, extra helper reactions, and we'll discuss how to control regiochemistry with various directing groups.
https://joechem.io/videos/26 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we look at how to determine whether something is or isn't aromatic, the criteria for aromaticity, and what it means energetically to be aromatic. We also go through the same topics for antiaromaticity as well.
https://joechem.io/videos/27 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). Summary of all the mechanisms http://worksheets.joechem.io/worksheets/EAS-Mechanisms.pdf In this video, we look at a bunch of EAS reactions (aka adding stuff to benzene rings). The mechanisms covered in this video are: Chapters: 0:00 Intro 1:44 Cl2/AlCl3 6:20 Br2/FeBr3 10:24 HNO3/H2SO4 15:40 SO3/H2SO4 19:31 Friedel Crafts Alkylation 24:50 Friedel Crafts Acylation I included them all in ONE video because I wanted to highlight how SIMILAR all of the mechanisms are. But the order above^ is how they appear in the video.
https://joechem.io/videos/28 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we look at directing groups and how substituents off of benzene rings can direct newly added groups ortho/para or meta.
https://joechem.io/videos/192 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). Now armed with the knowledge of ortho/para and meta directing, we turn our attention to how groups activate and deactivate benzene, either through resonance or induction. We'll talk about how halogens, while they direct ortho/para, ultimately deactivate benzene rings through induction. And we'll talk about how reactions proceed when you have multiple benzene rings.
https://joechem.io/videos/123 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we'll review all the reactions we can use to reduce benzylic carbonyls as well as how we can use KMnO4 to oxidize benzylic substituents. This video is loosely related to the other EAS helper reactions covered in https://joechem.io/videos/29
https://joechem.io/videos/29 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we look at other EAS/Benzene reactions that are very helpful transformations (will be super useful in synthesis and necessary to know for predicting the product type questions).
https://joechem.io/videos/191 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we again hone in on the benzylic position. Specifically we will look at the various ways we can perform oxidation at the benzylic position. I know we already covered the KMnO4 oxidation earlier, but I originally made this video for the section that dives deeper into benzene chemistry, where the MnO2 oxidation is introduced. So, now you know the KMnO4 oxidation twice as well :)
https://joechem.io/videos/30 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we do synthesis practice with benzene and EAS reactions.
https://joechem.io/videos/124 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we'll look at one more EAS synthesis-like/complete the reaction problem that I think ties a lot of EAS related ideas together as well as involves older knowledge from Ochem I.