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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 ...
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:
As originally determined by Staudinger, [7] oxalyl chloride reacts with water giving off gaseous products only: hydrogen chloride (HCl), carbon dioxide (CO 2), and carbon monoxide (CO). [9] (COCl) 2 + H 2 O → 2 HCl + CO 2 + CO. Other acyl chlorides hydrolyze with formation of hydrogen chloride and the original carboxylic acid.
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.
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.
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 chloroformates and acyl chlorides are similar. Representative reactions are: Reaction with amines to form carbamates: [2] ROC(O)Cl + H 2 NR' → ROC(O)-N(H)R' + HCl. Reaction with alcohols to form carbonate esters: ROC(O)Cl + HOR' → ROC(O)-OR' + HCl. Reaction with carboxylic acids to form mixed anhydrides:
Chloroacetyl chloride is bifunctional—the acyl chloride easily forms esters [4] and amides, while the other end of the molecule is able to form other linkages, e.g. with amines. The use of chloroacetyl chloride in the synthesis of lidocaine is illustrative: [ 5 ]