Ketones can be converted to esters through the Baeyer–Villiger oxidation, where a ketone reacts with a peracid (like mCPBA) to insert an oxygen atom next to the carbonyl, forming an ester. Notice that the more substituted alkyl group of … Read more
The Beckmann rearrangement is a reaction in which a ketone is first converted to an oxime, which, under acidic or Lewis acidic conditions, rearranges into an amide. This reaction is closely related to the Hofmann, Schmidt, and Curtius rearrangements, as … Read more
Baeyer-Villiger Oxidation The Baeyer-Villiger oxidation is a rearrangement reaction that converts ketones to esters using peroxycarboxylic acids, such as meta-chloroperoxybenzoic acid (mCPBA). The Baeyer–Villiger oxidation can also convert aldehydes into carboxylic acids, but let’s be honest, including that as a key use … Read more
In the previous post, we talked about the Hofmann Rearrangement, which is the conversion of primary amides to primary amines: Notice that the carbon chain of the product is shorter by one atom because of the decarboxylation that … Read more
In this post, we’ll talk about the Hofmann rearrangement, a reaction that’s used to convert primary amides into primary amines. We know from earlier discussions that amides are generally converted to amines by reducing them with LiAlH4. … Read more
In the previous post, we discussed ring expansion rearrangements where 4 and 5-membered rings were transformed into more stable larger rings. Sometimes, the process goes in reverse direction, and larger rings are transformed into smaller rings. These are … Read more
Ring Strain and Ring Expansion The title of today’s discussion contains two keywords: Ring Expansion and Rearrangement. So, what are those? A ring expansion is the transformation of a smaller ring to a larger ring. A rearrangement is a change … Read more
The SN1 mechanism is a unimolecular process, which means only the substrate participates in the rate-determining step of the reaction. The rate-determining step is the loss of the leaving group, which forms a carbocation. There are a few main features … Read more
Markovnikov’s Rule In the previous post, we talked about the addition reaction of hydrogen halides (HCl, HBr, and HI) to alkenes, and learned about Markovnikov’s rule, which states that in these reactions, the halogen adds to the more substituted carbon … Read more
When 1,2-diols (vicinal diols) are treated with acid, a rearrangement takes place, and the diol is transformed to a ketone. This reaction is known as the pinacol rearrangement since pinacol is the simplest diol capable of undergoing such … Read more
