We have seen that LiAlH4 is one of the most powerful reducing agents and can be used to reduce many functional groups, such as aldehydes, ketones, esters, nitriles, and even carboxylic acids. Many of these reductions can also be achieved … Read more
We have seen many nucleophilic addition reactions to aldehydes and ketones, including those of amines. So, when we imagine an amine reacting with an aldehyde or ketone, we immediately recall the C=N bond, which implies formation of an imine, also … Read more
The amine functional group is one of the most common and important nitrogen-containing groups in organic chemistry. Amines are derivatives of ammonia (NH₃), where one or more hydrogen atoms are replaced by alkyl or aryl groups. Amines play central … Read more
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
Nucleophilic Additions to the Carbonyl Group In this chapter on aldehydes and ketones, we begin to see a new type of mechanism originating from the polar nature of the C=O carbonyl bond. When we say “different,” that is mainly compared … Read more
We have seen that alcohols can be converted to amines by converting the OH into a good leaving group and reacting the substrate with an amine: The reverse process is more challenging because NH2 is even a worse … Read more
Reductive amination is used for preparing amines from aldehydes and ketones. All we need is to mix an amine with an aldehyde or ketone in the presence of sodium cyanoborohydride (NaBH3CN) at lower pH levels: So, how does … Read more
We have seen in many reactions that amines are quite good nucleophiles and strong bases, and therefore, sometimes, they need to be protected to allow for transformations of other functional groups. Perhaps the most common strategy to protect an amino … Read more
Although amines are considered weak bases, in general, their presence in neutral organic molecules makes the basic sites in those structures because they are stronger bases and nucleophiles than other neutral organic compounds. For example, in DNA, there are aromatic … Read more
In the previous post, we talked about the Hofmann reaction where amines are converted into quaternary ammonium salts and later to alkenes. Remember, amines, and especially the conjugate bases of amines, are strong bases and therefore, they are poor leaving … Read more
