Norbornane is a bicyclic compound (bicyclo[2.2.1]heptane) with a rigid, saturated framework. Norbornene is its corresponding alkene, containing a double bond that makes it reactive toward typical electrophilic addition reactions. Norbornanone is a ketone derivative, where the carbonyl group undergoes nucleophilic … Read more
Loperamide is an antidiarrheal medication best known under the brand name Imodium. It works by activating μ-opioid receptors in the intestinal tract, which slows down gut movement and reduces the frequency of bowel movements. Unlike other opioids, Loperamide does not … Read more
In this post, we will discuss and show the mechanisms of some important reactions of lactones and lactams, such as their preparation, acid- and base-catalyzed hydrolysis, and reduction by LiAlH4. We will also go over the Grignard reaction of lactones. … Read more
So far, we’ve seen a variety of nucleophiles in organic chemistry – halides, hydroxides, alkoxides, thiols, etc. Most of these nucleophiles contain heteroatoms like oxygen, nitrogen, or sulfur, but nucleophiles can also be carbon-based, and these are among the most … Read more
There are several ways to prepare esters, and in this lesson, we’ll go over the most common ones you’ll see in organic chemistry. The most famous is the Fischer esterification, where a carboxylic acid is reacted with an alcohol under … Read more
Acid chlorides can be reduced to aldehydes by lithium tri(t-butoxy) aluminum hydride (LiAl(OtBu)₃H): So, why not use NaBH₄ or LiAlH₄ for reducing acid chlorides to aldehydes? Remember that acid chlorides are the most reactive derivatives of carboxylic acids, … Read more
We have seen in many examples how Grignard and organolithium reagents react with various carbonyl compounds such as aldehydes, ketones, esters, and more. So, let’s discuss what happens when we react a Grignard or organolithium reagent with carbon dioxide. Although … Read more
This content is for registered users only. Click here to Register! By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction … Read more
We have seen that carboxylic acids can be reduced with LiAlH4 and boranes to primary alcohols. We also know that esters, nitriles, and acid chlorides can be reduced to aldehydes using DIBAL or at lowered temperatures (typically -78 oC): … Read more
Amides are the least reactive derivatives of carboxylic acids, so reducing them requires using the strong reducing agent LiAlH4. The reduction converts primary, secondary, tertiary cyclic, and acrylic amides to corresponding amines: The Mechanism of Amide Reduction by … Read more
