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Carbonyl compounds are more acidic than alkanes for the same reason that carboxylic acids are more acidic than alcohols. In both cases, the anions are stabilized by resonance. Enolate ions differ from carboxylate ions, however, in that their two resonance forms are not equivalent- the form with the negative charge on oxygen is lower in energy ...
Fischer esterification is an acyl substitution reaction based on the electrophilicity of the carbonyl carbon and the nucleophilicity of an alcohol. Carboxylic acids tend to be deprotonated by nucleophiles, which gives an unreactive carboxylate.
The loss of a proton gives the substitution product, 6. Because the last step involves the loss of a proton, nucleophilic acyl substitution reactions are considered catalytic in acid. Also note that under acidic conditions, a nucleophile will typically exist in its protonated form (i.e. H−Z instead of Z −).
Similarly, the α-bromocarboxylic acid undergo nucleophilic substitution with ammonia to give the amino acid, [3] The Darzens reaction involves a ketone or aldehyde with an α-haloester in the presence of a base to form an α,β-epoxy ester, also called a "glycidic ester". [4] The reaction process begins with deprotonation at the halogenated ...
The reaction mechanism of the Mitsunobu reaction is fairly complex. The identity of intermediates and the roles they play has been the subject of debate. Initially, the triphenyl phosphine (2) makes a nucleophilic attack upon diethyl azodicarboxylate (1) producing a betaine intermediate 3, which deprotonates the carboxylic acid (4) to form the ion pair 5.
First, in the presence of a chiral nucleophilic catalyst, by the action of an appropriate carboxylic acid anhydride on a racemic aliphatic carboxylic acid, the corresponding MA is produced, resulting in the kinetic resolution of the racemic aliphatic carboxylic acid after having been subjected to reaction with achiral alcohol. [9]
When ortho substitution occurs in benzoic acid, steric hindrance causes the carboxyl group to twist out of the plane of the benzene ring. The twisting inhibits the resonance of the carboxyl group with the phenyl ring, leading to increased acidity of the carboxyl group.
Reaction mechanism for the amine formation from a carboxylic acid via Schmidt reaction. In the reaction mechanism for the Schmidt reaction of ketones , the carbonyl group is activated by protonation for nucleophilic addition by the azide, forming azidohydrin 3 , which loses water in an elimination reaction to diazoiminium 5.
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