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
Let’s address two common exam questions: comparing the SN2 and E2 rates of two isomeric cyclohexanes and determining the major product in those reactions. The first thing you need to remember here is that both SN2 and E2 … Read more
The reactivity of epoxides is due to the high ring strain of three-membered rings. The reactions of epoxides lead to the ring opening, forming an alcohol with a variety of other functional groups in the product. We have seen, in … 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
Halohydrins are compounds containing a vicinal (adjacent) halogen and a hydroxyl groups. Halohydrins are prepared by the traction of alkenes with halogens in the presence of water: Recall that in neutral solvents such as CCl4 and DCM, the … Read more
