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General chemical structure of an acyl chloride. 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 ...
Strictly speaking, this reaction results in the formation of a rhodium carbonyl complex rather than free carbon monoxide. The catalytic cycle is assumed to involve oxidative addition of the aldehyde (or acid chloride) to gives a 16e acyl Rh(III)-hydride intermediate, which undergoes migratory extrusion of CO proceed to form an 18-electron d6 Rh ...
The reactivity of these five classes of compounds covers a broad range; the relative reaction rates of acid chlorides and amides differ by a factor of 10 13. [2] A major factor in determining the reactivity of acyl derivatives is leaving group ability, which is related to acidity.
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.
The general formula for such an acyl halide can be written RCOX, where R may be, for example, an alkyl group, CO is the carbonyl group, and X represents the halide, such as chloride. Acyl chlorides are the most commonly encountered acyl halides, but acetyl iodide is the one produced (transiently
An alternative, involving the formation of an acylium ion, becomes more important when the reaction takes place in concentrated acid (>90% sulfuric acid). [7] (In the Curtius rearrangement, sodium azide and an acyl chloride are combined to quantitatively generate the acyl azide intermediate, and the rest of the reaction takes place under ...
Substituted ketenes can be prepared from acyl chlorides by an elimination reaction in which HCl is lost: Formation of a ketene from an acyl chloride. In this reaction, a base, usually triethylamine, removes the acidic proton alpha to the carbonyl group, inducing the formation of the carbon-carbon double bond and the loss of a chloride ion:
Acetyl chloride is used for acetylation reactions, i.e., the introduction of an acetyl group. Acetyl is an acyl group having the formula −C(=O)−CH 3. For further information on the types of chemical reactions compounds such as acetyl chloride can undergo, see acyl halide.