Esters can be converted into primary, secondary, and tertiary amides by an aminolysis reaction with ammonia, primary amine, and a secondary amin,e respectively: The reaction goes by a nucleophilic addition-elimination mechanism, and alkoxy groups (RO–), being poor leaving … Read more
Reduction of Acyl Chlorides to Alcohols Acid chlorides can be reduced to alcohols by lithium aluminum hydride (LiAlH4) and sodium borohydride (NaBH4). In both reactions, there is an aldehyde intermediate formed and therefore, the reducing agent is used … Read more
Alright, so we learned about the Fischer esterification from carboxylic acids and alcohols and their hydrolysis in acidic or basic conditions but what is transesterification? Transesterification is the conversion of one ester to another – simple: Just like … Read more
We have seen that all the steps in the Fischer esterification are reversible and the equilibrium is shifted toward the ester product by using an excess of alcohol. This nature of the reaction allows to hydrolyze esters back into a … Read more
Fischer esterification is the acid-catalyzed reaction of carboxylic acids and alcohols: Before we get into the details of this reaction, remember that there are other ways of preparing esters. For example, the carboxylic acid can be converted into … Read more
Acyl chlorides are very useful in reactions with organometallics because they can selectively be converted into alcohols or ketones. For example, Grignard reagents will react with acyl chlorides to produce alcohols, while organocuprates (Gilman’s), also known as lithium dialkyl cuprates, … 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
Acyl chlorides can be prepared by reacting carboxylic acids with thionyl chloride (SOCl2), phosphorous trichloride (PCl3) or phosphorous pentachloride (PCl5): In the bases of this transformation is the conversion of the OH group into a good leaving. For … Read more
One of the most common carboxylic acids is the acetic acid which has a wide range of application starting from vinegar and going all the way to the synthesis of organic materials including vinyl acetate, which is used as a polymer … Read more
Carboxylic acid derivatives practice problems This is a comprehensive practice problem covering most of the nucleophilic acyl substitution reactions of carboxylic acids and their derivatives. Here is the content of this 1-hour video for the practice problem solutions: The detailed … Read more
