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
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
Alkynes and nitriles are structurally similar, so let’s discuss how we can replace one of the carbons in the alkyne with a nitrogen: When one of the carbons is replaced, the carbon chain will be shortened by one. … 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
Epoxides are three-membered rings containing an oxygen atom. They are associated with high ring strain, and this is the basis of their reactivity towards nucleophiles despite lacking a good leaving group. The ring strain is a combination of two destabilizing factors: angle … Read more
In the previous post, we discussed the ring-opening reactions of epoxides with strong and weak nucleophiles. Using this information, try solving the following practice problems.
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
A variety of reactions that we have seen earlier can be used for preparing amines. The most straightforward would look like an SN2 reaction of an alkyl halide with ammonia or an amine: The main drawback of this … Read more
Michael reactions are conjugate-addition reactions of doubly stabilized enolates such as malonic ester, acetoacetic ester, and the like with ɑ, β-unsaturated carbonyl compounds: So, the Michael reaction is a particular type of conjugate addition reaction that ɑ, β-unsaturated … Read more
In the previous post, we talked about the acetoacetic ester synthesis, which is used for preparing ketones having one or two alkyl groups on the ɑ position: Another way to look at this reaction is to say that … Read more
