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Anhydrides experience even weaker resonance stabilization, since the resonance is split between two carbonyl groups, and are more reactive than esters and amides. In acid halides, there is very little resonance, so the energetic penalty for forming a tetrahedral intermediate is small.
A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O)) 2 O. Symmetrical acid anhydrides of this type are named by replacing the word acid in the name of the parent carboxylic acid by the word anhydride. [2] Thus, (CH 3 CO) 2 O is called acetic ...
An acid anhydride is a type of chemical compound derived by the removal of water molecules from an acid. In organic chemistry, organic acid anhydrides contain the functional group −C(=O)−O−C(=O)−. Organic acid anhydrides often form when one equivalent of water is removed from two equivalents of an organic acid in a dehydration reaction.
Like most acid anhydrides, the carbonyl carbon atom of acetic anhydride has electrophilic character, as the leaving group is carboxylate. The internal asymmetry may contribute to acetic anhydride's potent electrophilicity as the asymmetric geometry makes one side of a carbonyl carbon atom more reactive than the other, and in doing so tends to ...
Acyl chlorides are used to prepare acid anhydrides, amides and esters, by reacting acid chlorides with: a salt of a carboxylic acid, an amine, or an alcohol, respectively. Acid halides are the most reactive acyl derivatives, and can easily be converted into any of the others. Acid halides will react with carboxylic acids to form anhydrides.
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Acyl halides are rather reactive compounds often synthesized to be used as intermediates in the synthesis of other organic compounds. For example, an acyl halide can react with: water, to form a carboxylic acid. This hydrolysis is the most heavily exploited reaction for acyl halides as it occurs in the industrial synthesis of acetic acid.