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
There are several ways of converting alcohols to alkyl halides. The most common, and perhaps the one that covers nuances of SN1 and SN2 reactions is the use of HX acids (HCl, HBr, HI), so let’s start with that. The … Read more
Let’s discuss some strategies for converting alkyl halides to aldehydes and ketones. Converting the alkyl halide to an alcohol and oxidizing the latter to an aldehyde or ketone requires the least number of topics to have covered, so let’s start … Read more
Aldehydes and ketones are carbonyl compounds, and the carbon here is in a relatively high oxidation state: Notice that the oxidation state of the carbon decreases with the number of hydrogens connected to it. On the contrary, the … Read more
Let’s discuss an important and perhaps the most common way of converting aldehydes and ketones to amines, known as reductive amination. Before going into the details of reductive amination, let’s recall that amines are not formed by “simply” reacting aldehydes … Read more
Amides are derivatives of carboxylic acids, therefore, one strategy to convert aldehydes to amides is by first oxidizing them to carboxylic acids. Once we have the carboxylic acid, we can subject it to condensation with amines using a coupling agent … Read more
Let’s discuss a few strategies for converting alkenes to carboxylic acids that allow to increase the length of the carbon chain, decrease it, and keep it the same as well: Alkenes to Carboxylic Acids: Keeping the Length of … Read more
Direct Conversion of Acid Chlorides to Ketones Acid chlorides also known as acyl chlorides (ROCl) can be converted to ketones in direct and indirect transformations. The direct conversation is achieved by their reaction with organocuprates (Gilman reagent – R2CuLi). … Read more
Alcohols can be oxidized to aldehydes and ketones using a variety of oxidizing agents. The outcome of the oxidation depends both on the oxidizing agent and the structure of the alcohol. Recall from the oxidation states of organic compounds that … 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
