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
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
Diisobutylaluminium hydride, also known as (DIBAL, DIBALH, DIBAL-H or DIBAH) is a bulky reducing agent that is mainly used for converting esters and nitriles to aldehydes. The reaction is carried out at lower temperatures (typically -78 oC as that is the … Read more
Carboxylic acids can be reduced to primary alcohols using an excess of strong reducing agents such as lithium aluminum hydride (LiAlH4 or LAH). As sodium borohydride (NaBH4) is the most common reducing agent we learn about together with … Read more
Let’s discuss two strategies for preparing nitriles via substitution and dehydration reactions. Synthesis of Nitriles via Substitution Reactions To prepare a nitrile via a substitution reaction, we do an SN2 substitution of alkyl halides, mesylates, or tosylates with … Read more
Direct Conversion of Acid Chlorides to Ketones Acid chlorides also known as acyl chlorides (ROCl) can be converted to ketones in direct and indirect transformations. The direct conversation is achieved by their reaction with organocuprates (Gilman reagent – R2CuLi). … 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
There are a few ways of converting nitriles to amides. One of them is the sure way as it imposes no risk of your instructor counting it as invalid and taking some or all your points off. This is the … Read more
Primary amides can be converted to aldehydes and ketones via nitriles. So, the first thing we need here is a strong dehydrating agent such as SOCl2, P2O5, and POCl3 to convert the amide to a nitrile: Amides to Aldehydes … Read more
