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Acyl chlorides are used to prepare acid anhydrides, amides and esters, by reacting acid chlorides with: a salt of a carboxylic acid, an amine, or an alcohol, respectively. Acid halides are the most reactive acyl derivatives, and can easily be converted into any of the others.
If further reduction does take place, it will create a primary alcohol which would then react with the remaining acyl chloride to form an ester. Rosenmund catalyst can be prepared by reduction of palladium(II) chloride solution in the presence of BaSO 4. Typical reducing agent is formaldehyde. [5]
Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by treating potassium acetate with phosphoryl chloride. [4]Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as phosphorus trichloride (PCl 3), phosphorus pentachloride (PCl 5), sulfuryl chloride (SO 2 Cl 2), phosgene, or thionyl chloride (SOCl 2).
A molecule can have more than one acyl halide functional group. For example, "adipoyl dichloride", usually simply called adipoyl chloride, has two acyl chloride functional groups; see the structure at right. It is the dichloride (i.e., double chloride) of the 6-carbon dicarboxylic acid adipic acid.
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:
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.
In chemistry, acylation is a broad class of chemical reactions in which an acyl group (R−C=O) is added to a substrate. The compound providing the acyl group is called the acylating agent. The substrate to be acylated and the product include the following: alcohols, esters; amines, amides; arenes or alkenes, [1] ketones
Pseudoephedrine is reacted with a carboxylic acid, acid anhydride, or acyl chloride to give the corresponding amide. The α-proton of the carbonyl compound is easily deprotonated by a non-nucleophilic base to give the enolate, which can further react.