Gilman reagents are organocuprates with a general formula of R2CuLi. To be more specific, these are lithium dialkylcuprates. You can look at them as “weaker” Grignard or organolithium reagents, meaning they are less reactive but also unique in a few … Read more
Preparation of Nitriles Nitriles can be prepared by substitution reactions of alkyl halides with cyanide salts: These are nucleophilic substitution reactions and we introduce the nitrile group by using the nucleophilicity of the cyanide ion. In a similar … Read more
We know that aldehydes and ketones react with one equivalent of Grignard reagents, producing secondary and tertiary alcohols, respectively. Esters, on the other hand, react with two equivalents of Grignard reagents, producing tertiary alcohols: What happens is we have … Read more
There are two main strategies we can use to convert alkyl halides to carboxylic acids: 1) Oxidizing the carbon connected to the halogen, 2) Introducing the COOH group, thus increasing the length of the carbon chain: For the … 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
In this conversion series, we mention how nitriles can be converted to ketones and aldehydes. Nitriles are converted to ketones by both Grignard and organolithium reagents: The new C-C bonds are formed by nucleophilic addition of the organometallic … Read more
Preparation of Phenols Phenols can be prepared industrially by a substitution reaction of aryl halides under extreme conditions: This is a type of nucleophilic aromatic substitution via a benzyne intermediate: Milder conditions suitable for laboratory preparation … 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
In the previous post, we discussed the ring-opening reactions of epoxides with strong and weak nucleophiles. Using this information, try solving the following practice problems.
Michael reactions are conjugate-addition reactions of doubly stabilized enolates such as malonic ester, acetoacetic ester, and the like with ɑ, β-unsaturated carbonyl compounds: So, the Michael reaction is a particular type of conjugate addition reaction that ɑ, β-unsaturated … Read more
