Halonium ions are structures where a halogen atom is connected to two alkyl groups: In your organic chemistry class, you are only going to worry about a specific type of halonium ion where the halogen is part of … Read more
In this article, we will summarize and compare the reactions of Grignard (RMgX), Gilman (R2CuLi), and organolithium (RLi) reagents. Let’s first see what unites and makes their properties similar or at least creates a pattern for us to predict the … Read more
Epoxides undergo ring-opening reactions under both acidic and basic conditions. Let’s clarify that by “basic conditions” we refer to a greater class of epoxide ring-openings when they are reacted with good nucleophiles. This includes a number of them such as … 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
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
Epoxides are three-membered rings containing an oxygen atom. They are associated with high ring strain, and this is the basis of their reactivity towards nucleophiles despite lacking a good leaving group. The ring strain is a combination of two destabilizing factors: angle … Read more
We have seen many times when discussing the SN2 mechanism that ethers are common products of nucleophilic substitution reactions. They are synthesized by reacting alkyl halides or other substrates with good leaving groups with alkoxides: This method of … Read more
From Acid-Catalyzed Hydration of Alkenes In the previous post, we talked about the acid-catalyzed hydration of alkenes, which, in general, is a “Markovnikov” addition of water, giving the corresponding alcohol. A quick reminder, Markovnikov’s rule is followed when the X component … Read more
