We have discussed earlier that esters can be hydrolyzed under acidic or basic conditions to give carboxylic acids and alcohols. Lactones behave in an analogous way, except that being cyclic esters, their hydrolysis leads to ring opening and … Read more
We have seen earlier that esters react with two equivalents of Grignard reagent to form tertiary alcohols after acidic workup. The reaction occurs through two successive nucleophilic additions: the first addition forms a tetrahedral intermediate that collapses by expelling the … Read more
We have seen that amides can be hydrolyzed to carboxylic acids and amines under acidic or basic conditions. Lactams are cyclic amides, and the amino and carboxyl groups are part of the same molecule; therefore, the products of … Read more
We have seen that the reduction of lactones with LiAlH₄ proceeds through ring opening and ultimately gives diols after two consecutive hydride additions. A very similar hydride reduction can also be applied to lactams, although the outcome and key mechanistic … Read more
We have seen that esters can be reduced to alcohols by lithium aluminum hydride (LiAlH₄) through two consecutive additions of hydride ions to the carbonyl carbon. The mechanism starts with nucleophilic attack of hydride on the ester carbonyl, … Read more
Introduction to Lactams Lactams are cyclic amides, and they are classified according to the size of the ring containing the amide group. The naming uses Greek letters that indicate how many carbon atoms lie between the nitrogen and the carbonyl … Read more
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
