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
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
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
Decarboxylation is the loss of carbon dioxide upon heating, typically characteristic of carboxylic acids with a β-carbonyl group. These are most often beta-keto acids, malonic acid, or its derivatives: Carboxylic acids by themselves are very stable and do … Read more
Remember, earlier, we discussed the Friedel–Crafts acylation reaction, which is used for preparing aryl ketones by reacting aromatic compounds with an acyl halide in the presence of a Lewis acid catalyst. Now, here is a question: how can … 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
In the previous post, we discussed the alkylation reactions of enolates, which are one of the most important transformations in carbonyl chemistry. Enolates are typically formed from carbonyl compounds, but they are not limited to aldehydes and ketones. Similar enolate-type … Read more
In the previous post, we talked about the alpha halogenation of aldehydes and ketones and its application in organic synthesis. So, if you have already gone over this material, go ahead and work on these practice problems. The second part … Read more
Acyl chlorides, being the most reactive among carboxylic acid derivatives, undergo a wide variety of nucleophilic acyl substitution reactions. A quick reminder, in a nucleophilic acyl substitution, the leaving group is replaced by a nucleophile by the addition-elimination mechanism: … Read more
