The Nucleophilic acyl substitution reaction:-
The fact that the atom adjacent to the carbonyl carbon in carboxylic acid derivatives is an electronegative heteroatom – rather than a carbon like in ketones or a hydrogen like in aldehydes - is critical to understanding the reactivity of these functional groups. The carboxylic acid derivatives are attacked from one side of their trigonal planar carbonyl carbon by a nucleophile, converting this carbon to tetrahedral (sp3) geometry. In carboxylic acid derivatives, the acyl X group is a leaving group. the tetrahedral product formed from attack of the nucleophile on the carbonyl carbon is not the product: it is a reactive intermediate. The tetrahedral intermediate rapidly collapses: the carbon-oxygen double bond re-forms, and the acyl X group is expelled.Carboxylic acids have conjugation which makes them stable i.e. unreactive or less reactive, whereas acid halides don't have such possibility and due to electronegative nature of halide groups the carbon becomes more electrophilic hence more reactive towards any nucleophilic attack. So the overall reactivity order is:- The acid chloride is most reactive and the amide is least reactive.
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Provide three examples (both structure and name for each case) for the following carboxylic acid and its derivatives (a) Carboxylic acid (b) Acid halide (c) Acid anhydride (d) Ester (e) Thioester (0) Amide 1. 6x3-18 2. Write a preparation method for one compound from each category in question 1 . 6x2-12 The following two are the general reaction mechanisms for carbonyl group containing compounds. What is the difference between them? Write mechanism from a reaction describe in question 2. 3....