jOeCHEMists, I think you're going to find this section as a breath of fresh air. As we exit the land of carboxlyic acids, we find ourselves tasked with learning chemistry associated with esters, acid halides, acid anhydrides, and amides. But, after spending lots of quality time with carboxylic acids, you're going to see an insane amount of similarity in the reactions we're about to do. When you nail down the addition-elimination mechanism, you're going to realize this series is basically that over and over again (with some exceptions, of course).
https://joechem.io/videos/74 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we look at the relative reactivities of these carboxylic acid derivatives (amides, esters, thioesters, acid anhydrides, and acid halides), comparing the quality of their built-in leaving groups and effect on the carbonyl carbon's electrophilicity.
https://joechem.io/videos/193 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link) In this video, we talk about both Hard and Soft Nucleophiles. We'll dive into what they are, the difference between the two, and go over common Hard and Soft nucleophiles you'll see/encounter. Related video: https://joechem.io/videos/43 - The Michael Addition + 1,4 Additions with Soft Nucleophiles
https://joechem.io/videos/75 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we look at addition-elimination reactions with acid halides functional groups and how these reactions differ (in mechanism and product) when a hard vs soft nucleophile is used in the addition-elimination pathway.
https://joechem.io/videos/76 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we look at addition-elimination reactions with acid anhydride functional groups and how these reactions differ (in mechanism and product) when a hard vs soft nucleophile is used in the addition-elimination pathway.
https://joechem.io/videos/77 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we look at various reactions involving the ester functional group, such as: 1.) Hydrolysis (breaking the ester up with some water) 2.) Transesterification 3.) Attacking an ester with a "hard" nucleophile (such as a Grignard or LAH)*
https://joechem.io/videos/78 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we look at various reactions involving the amide functional group, such as: 1.) Hydolysis of amides (breaking up an amide w/ H2O) 2.) Reduction of an amide to an amine with LiAlH4
https://joechem.io/videos/194 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link) In this video, we'll talk about the various Hydride containing reagents we can use to reduce carboxylic acid derivatives. We'll identify the differences in reactivity and the benefits/drawbacks that each contain.
https://joechem.io/videos/136 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we talk about Nitriles and what happens when we reduce them. We'll look at two reducing agents, DIBAL and LAH and how, when in the presence of a nitrile, yields two different functional groups.
https://joechem.io/videos/135 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we delve into the lovely Hofmann Rerrangement. We'll discuss the reactant criteria, reagents needed, how to predict Hofmann Rearrangement products, and step through the mechanism itself.