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Acetyl chloride is a reagent for the preparation of esters and amides of acetic acid, used in the derivatization of alcohols and amines. One class of acetylation reactions are esterification, for example the reaction with ethanol to produce ethyl acetate and hydrogen chloride: CH 3 COCl + HO−CH 2 −CH 3 → CH 3 −COO−CH 2 −CH 3 + HCl
In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids (R−C(=O)OH). A specific example of an acyl chloride is acetyl chloride, CH 3 COCl.
Benzene is sufficiently nucleophilic that it undergoes substitution by acylium ions and alkyl carbocations to give substituted derivatives. Electrophilic aromatic substitution of benzene. The most widely practiced example of this reaction is the ethylation of benzene. Approximately 24,700,000 tons were produced in 1999. [73]
Some chloroacetyl chloride is also used to produce phenacyl chloride, another chemical intermediate, also used as a tear gas. [3] Phenacyl chloride is synthesized in a Friedel-Crafts acylation of benzene, with an aluminium chloride catalyst: [6] With anisole, it is used for the synthesis of venlafaxine.
For example, Friedel–Crafts acylation uses acetyl chloride (CH 3 COCl) as the agent and aluminum chloride (AlCl 3) as a catalyst to add an acetyl group to benzene: [2] Friedel-Crafts acylation of benzene by ethanoyl chloride. This reaction is an example of electrophilic aromatic substitution.
The Schotten–Baumann reaction is a method to synthesize amides from amines and acid chlorides: An example of a Schotten-Baumann reaction. Benzylamine reacts with acetyl chloride under Schotten-Baumann conditions to form N-benzylacetamide. Schotten–Baumann reaction also refers to the conversion of acid chloride to esters.
In IUPAC nomenclature, an acetyl group is called an ethanoyl group. An acetyl group contains a methyl group (−CH 3) that is single-bonded to a carbonyl (C=O), making it an acyl group. The carbonyl center of an acyl radical has one non-bonded electron with which it forms a chemical bond to the remainder (denoted with the letter R) of the molecule.
The reaction typically employs a strong Lewis acid, such as aluminium chloride as catalyst, to increase the electrophilicity of the alkylating agent. [6] This reaction suffers from the disadvantage that the product is more nucleophilic than the reactant because alkyl groups are activators for the Friedel–Crafts reaction. Consequently ...