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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.
This reaction is an example of electrophilic aromatic substitution. Acyl halides and acid anhydrides of carboxylic acids are also common acylating agents. In some cases, active esters exhibit comparable reactivity. All react with amines to form amides and with alcohols to form esters by nucleophilic acyl substitution.
A general acyl group (blue) in a ketone (top left), as an acylium cation (top centre), as an acyl radical (top right), an aldehyde (bottom left), ester (bottom centre) or amide (bottom right). ( R 1 , R 2 and R 3 stands for organyl substituent or hydrogen in the case of R 1 )
Here, a strong Lewis acid is required to generate either a carbocation from an alkyl halide in the Friedel-Crafts alkylation reaction or an acylium ion from an acyl halide. In the vast majority of cases, reactions that involve leaving group activation generate a cation in a separate step, before either nucleophilic attack or elimination.
Acid–base-catalysed hydrolyses are very common; one example is the hydrolysis of amides or esters. Their hydrolysis occurs when the nucleophile (a nucleus-seeking agent, e.g., water or hydroxyl ion) attacks the carbon of the carbonyl group of the ester or amide. In an aqueous base, hydroxyl ions are better nucleophiles than polar molecules ...
An ester of a carboxylic acid.R stands for any group (typically hydrogen or organyl) and R ′ stands for any organyl group.. In chemistry, an ester is a compound derived from an acid (organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group (−OH) of that acid is replaced by an organyl group (R ′). [1]
N-acyl amides are a general class of endogenous fatty acid compounds characterized by a fatty acyl group linked to a primary amine metabolite by an amide bond. Broadly speaking, N-acyl amides fall into several categories: amino acid conjugates (e.g., N-arachidonoyl-glycine), neurotransmitter conjugates (e.g., N-arachidonoyl-serotonin), ethanolamine conjugates (e.g., anandamide), and taurine ...
Hydrazones are susceptible to hydrolysis: R 2 C=N−NR' 2 + H 2 O → R 2 C=O + H 2 N−NR' 2. Alkyl hydrazones are 10 2 - to 10 3-fold more sensitive to hydrolysis than analogous oximes. [10] When derived from hydrazine itself, hydrazones condense with a second equivalent of a carbonyl to give azines: [11] R 2 C=N−NH 2 + R 2 C=O → R 2 C=N ...