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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).
For example, acetic acid boils at 118 °C, whereas acetyl chloride boils at 51 °C. Like most carbonyl compounds, infrared spectroscopy reveals a band near 1750 cm −1. The simplest stable acyl chloride is acetyl chloride; formyl chloride is not stable at room temperature, although it can be prepared at –60 °C or below. [2] [3]
Weak bases are better leaving groups than strong bases; a species with a strong conjugate acid (e.g. hydrochloric acid) will be a better leaving group than a species with a weak conjugate acid (e.g. acetic acid). Thus, chloride ion is a better leaving group than acetate ion. The reactivity of acyl compounds towards nucleophiles decreases as the ...
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 ]
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Where HV is the hydroxyl value; V B is the amount (ml) potassium hydroxide solution required for the titration of the blank; V acet is the amount (ml) of potassium hydroxide solution required for the titration of the acetylated sample; W acet is the weight of the sample (in grams) used for acetylation; N is the normality of the titrant; 56.1 is ...
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.
Trichloroacetyl chloride is the acyl chloride of trichloroacetic acid. It can be formed by reacting chlorine with acetyl chloride or acetaldehyde in the presence of activated charcoal, or by the isomerisation of tetrachloroethylene oxide via heating. It is used in the manufacture of pharmaceuticals and plant protection compounds. [4]