Let’s look at this conversion through the eyes of a student new to organic chemistry: amides are almost like amines, except they contain a carbonyl (C=O) group attached to the nitrogen.So, how can we add a carbonyl to the nitrogen? … Read more
Acid chlorides can be reduced to aldehydes by lithium tri(t-butoxy) aluminum hydride (LiAl(OtBu)₃H): So, why not use NaBH₄ or LiAlH₄ for reducing acid chlorides to aldehydes? Remember that acid chlorides are the most reactive derivatives of carboxylic acids, … 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
This content is for registered users only. Click here to Register! By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction … 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
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
