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
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
Primary amides can be converted to nitriles by strong dehydrating agents such as SOCl2, P2O5, and POCl3: Before going into the mechanisms of these reactions. Let’s first address one important question you might be wondering about. Why is … Read more
