Preparation of Amides Amides can be prepared from acyl chlorides, esters, and carboxylic acids. The most straightforward should be the reaction with acid chlorides since they are the most reactive carboxylic acid derivatives, and amines are good nucleophiles too. This … 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
Remember when discussing the substitution reactions, we said that the hydroxide ion (–OH) is a poor leaving group since it is quite a strong base. Therefore, the –OH cannot be expelled by a direct nucleophilic attack in an SN2 or … Read more
Thionyl chloride (SOCl2) and phosphorus tribromide (PBr3) can be used for converting primary and secondary alcohols to alkyl chlorides and alkyl bromides respectively: Both reactions have similar mechanisms with the idea of turning the OH into a good … Read more
