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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 ]
In organic chemistry, an acetyl group is a functional group denoted by the chemical formula −COCH 3 and the structure −C(=O)−CH 3. It is sometimes represented by the symbol Ac [5] [6] (not to be confused with the element actinium). In IUPAC nomenclature, an acetyl group is called an ethanoyl group.
The molar mass of atoms of an element is given by the relative atomic mass of the element multiplied by the molar mass constant, M u ≈ 1.000 000 × 10 −3 kg/mol ≈ 1 g/mol. For normal samples from Earth with typical isotope composition, the atomic weight can be approximated by the standard atomic weight [ 2 ] or the conventional atomic weight.
As an alternative, acetyl chloride and acetic anhydride can be used to generate a solution of the acid with lower water content. Peracetic acid is generated in situ by some laundry detergents . This is achieved by the action of bleach activators , such as tetraacetylethylenediamine and sodium nonanoyloxybenzenesulfonate , upon hydrogen peroxide ...
In 1853, chemist Charles Frédéric Gerhardt treated sodium salicylate with acetyl chloride to produce acetylsalicylic acid for the first time; [13]: 46–48 in the second half of the 19th century, other academic chemists established the compound's chemical structure and devised more efficient methods of synthesis.