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Acetic anhydride in a glass bottle. Acetic anhydride, like most acid anhydrides, is a flexible molecule with a nonplanar structure. [4] The pi system linkage through the central oxygen offers very weak resonance stabilization compared to the dipole-dipole repulsion between the two carbonyl oxygens. The energy barriers to bond rotation between ...
The structure of the acetoxy group blue. In organic chemistry, the acetoxy group (abbr. AcO or OAc; IUPAC name: acetyloxy [1]), is a functional group with the formula −OCOCH 3 and the structure −O−C(=O)−CH 3. As the -oxy suffix implies, it differs from the acetyl group (−C(=O)−CH 3) by the presence of an additional oxygen atom.
A Lewis base is also a Brønsted–Lowry base, but a Lewis acid does not need to be a Brønsted–Lowry acid. The classification into hard and soft acids and bases ( HSAB theory ) followed in 1963. The strength of Lewis acid-base interactions, as measured by the standard enthalpy of formation of an adduct can be predicted by the Drago–Wayland ...
The term "acetyl" was coined by the German chemist Justus von Liebig in 1839 CE to describe what he incorrectly believed to be the radical of acetic acid (the main component of vinegar, aside from water), which is now known as the vinyl group (coined in 1851 CE); "acetyl" is derived from the Latin acētum, meaning "vinegar."
A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O)) 2 O. Symmetrical acid anhydrides of this type are named by replacing the word acid in the name of the parent carboxylic acid by the word anhydride. [2] Thus, (CH 3 CO) 2 O is called acetic ...
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).
Donor number and donor acceptor scale measures polarity in terms of how a solvent interacts with specific substances, like a strong Lewis acid or a strong Lewis base. [8] The Hildebrand parameter is the square root of cohesive energy density. It can be used with nonpolar compounds, but cannot accommodate complex chemistry.
A major factor in determining the reactivity of acyl derivatives is leaving group ability, which is related to acidity. 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).