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
We have seen in many examples how Grignard and organolithium reagents react with various carbonyl compounds such as aldehydes, ketones, esters, and more. So, let’s discuss what happens when we react a Grignard or organolithium reagent with carbon dioxide. Although … 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
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
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
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
Both Grignard and organolithium reagents can be used to convert nitriles to ketones. The new C-C bonds are formed by nucleophilic addition of the organometallic reagents to the polar C-N triple bond. After protonation of the resulting anion, … Read more
Acyl chlorides are very useful in reactions with organometallics because they can selectively be converted into alcohols or ketones. For example, Grignard reagents will react with acyl chlorides to produce alcohols, while organocuprates (Gilman’s), also known as lithium dialkyl cuprates, … Read more
Carboxylic acid derivatives practice problems This is a comprehensive practice problem covering most of the nucleophilic acyl substitution reactions of carboxylic acids and their derivatives. Here is the content of this 1-hour video for the practice problem solutions: The detailed … Read more
Acetals are the protecting groups for aldehydes and ketones. They can be used, for example, when a selective reduction of an ester is needed in the presence of an aldehyde or a ketone: Remember, aldehydes are more reactive … Read more
