If after the aromaticity + benzene series you found yourself craving more aromatic adventures, then I have some good news: you're in the right spot for round two. In this section, we massively deepen our knowledge regarding the chemistry we can do with benzene derivatives. We'll talk about ipso substitutions, EAS reactions with phenol, various rearrangements, and a whole lot more. We're even going to see a triple bond INSIDE of a benzene ring. It sounds whack. It sounds crazy. But, just like everything else we've learned together, we're going to master it.
https://joechem.io/videos/151 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we revisit an old friend--the benzylic position. We will recap the versatility of the position, explaining why it is prime to participate in SN1, SN2, Radical Addition, and Acid-Base reactions.
https://joechem.io/videos/152 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.
https://joechem.io/videos/153 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we once again look at the benzylic position. Instead of oxidation, we'll take a trip down reduction lane. We'll see how we can use hydrogen gas to reduce the benzylic position when an ether is present.
https://joechem.io/videos/154 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we officially make our acquaintance with phenol. This video covers various characteristics/qualities of phenol and contains a quick detour into naming of phenol derivatives. We'll work extensively with phenol in this series, so understanding naming basics as well as phenol's characteristics will be key.
https://joechem.io/videos/155 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we'll add the ipso substitution to our arsenal of organic tools. We'll talk about the meaning of an ipso substitution, what to look for when identifying one, and the importance of having an ortho/para EWG substituent. In the next video (https://joechem.io/videos/156), we'll do a few examples based on what we learn about the ipso substitution.
https://joechem.io/videos/156 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we'll take our newly earned ipso substitution knowledge and put it to the test. This video contains three examples, two of which that are mechanistic and one ranking-type problem. But all three are good exercises in exploring NAS. For an introduction to the ipso substitution, check out: https://joechem.io/videos/155
https://joechem.io/videos/157 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we stay on the ispo substitution train. We'll look at attacking haloarenes, benzenes rings that have a halogen substituent, with nucleophiles. Depending on conditions, the mechanism for these attacks can go one of two ways. The first of the two mechanistic patterns is the one that we've already explored. In this video, we'll explore the second pathway.
https://joechem.io/videos/159 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we'll take a look at how to create phenols through a process called diazotization. While attacking a haloarene with hydroxide produces phenols, high temperatures and pressures are needed for that reaction to work. Diazotization creates arenediazonium ions which water can attack at much milder temperatures and pressures. We'll take a look at the diazotization mechanism and how it helps us create phenols.
https://joechem.io/videos/160 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we'll take a look at phenols through the lens of being an alcohol. Sure phenol is special--it has an aromatic ring and that gives it super cool properties/characteristics. However, we can't forget that its an alcohol, so we'll look at some reactions that we've done in the past with other alcohols.
https://joechem.io/videos/161 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we'll lean on our previous benzene chemistry knowledge as we look at EAS rxns with phenol. Since the -OH group is a strong EDG, phenol directs additional groups in an ortho/para fashion. However, there is one thing to watch out for when doing Friedel-Crafts Acylations--check the video to find out what.
https://joechem.io/videos/162 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we'll take a look how we can use a phenoxide ion (phenol following deprotonation) to attack formaldehyde. This process is called hydroxymethylation, and in the case of phenol, it produces both ortho & para quinomethane. After we deep dive on the hydroxymethylation mechanism, we'll then see what other chemistry we can do with the quinomethanes produced.
https://joechem.io/videos/163 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we'll master the Kolbe Rxn. The Kolbe Rxn is when a phenoxide ion (deprotonated phenol) attacks carbon dioxide. We'll walk through the mechanism (which is short and sweet) and be pros at this reaction in no time.
https://joechem.io/videos/164 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we'll take a look at the Claisen Rearrangement. We'll discuss how to spot a Claisen Rearrangement as well as the concerted mechanism to correct predict the product when one occurs. Across the two examples in this video, you'll be a pro at Claisen Rearrangements in no time.
https://joechem.io/videos/165 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we'll take a look at the Cope Rearrangement. If you're wondering, "well, this looks an awful like the Claisen Rearrangement Joe talked about in https://joechem.io/videos/164 ??? What the heck?" Guess what: You're right! It is VERY similar. We'll take our knowledge from Claisen Rearrangements and master the Cope Rearrangement in two examples. Let's get it.