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
Amides are the least reactive derivatives of carboxylic acids, so reducing them requires using the strong reducing agent LiAlH4. The reduction converts primary, secondary, tertiary cyclic, and acrylic amides to corresponding amines: The Mechanism of Amide Reduction by … 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
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
Preparation of Aniline There are a few main ways of preparing aniline: Reduction of the Nitro Group We can add a nitro group to benzene or its derivative via a standard nitration using HNO3 and H2SO4, and then reduce the … 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 this post, we will talk about the synthesis of amides using DCC and EDC coupling agents. Before getting into the details, let’s first discuss a couple of strategies for preparing amides without using any fancy coupling agent. First, considering … Read more
In the following practice problems, the reactions and different ways of preparing amines will be discussed. Keep in mind that aside from the reactions specifically related to amines, such as the Gabriel amine synthesis, there are transformations that will require … Read more
