Acetyl Chloride

Topics: Carboxylic acid, Acyl chloride, Functional group Pages: 2 (371 words) Published: January 20, 2012
Acetyl chloride, CH3COCl, also known as ethanoyl chloride or acyl chloride, is an acid chloride derived from acetic acid. It belongs to the class of organic compounds called acyl halides. It is a colorless liquid. Acetyl chloride does not exist in nature, because contact with water would hydrolyze it into acetic acid and hydrogen chloride. In fact, if handled in open air it gives off white smoke owing to the hydrolysis from the moisture in the air. The "smoke" is actually small droplets of hydrochloric acid formed by hydrolysis.

Acetic anhydride dissolves in water to approximately 2.6% by weight.[10] Aqueous solutions have limited stability because, like most acid anhydrides, acetic anhydride hydrolyses to give acetic acid:[11] (CH3CO)2O + H2O → 2 CH3CO2H

Aminolysis is any chemical reaction in which a molecule is split into two parts by reacting with a molecule of ammonia or an amine. An example of an aminolysis reaction is the replacement of a halogen in an alkyl group (R-X) by an amine (R'-NH2) and the elimination of hydrogen halide (HX). R-X + R'-NH2 → R-NH-R' + HX

Another common example is the reaction of a primary amine or secondary amine with a carboxylic acid or with a carboxylic acid derivative to form an amide. This reaction is widely used, especially in the synthesis of peptides. On the simple addition of an amine to a carboxylic acid, a salt of the organic acid and base is obtained. To overcome this, the carboxylic acid first needs to be "activated". This is usually done by converting the acid into a more reactive derivative (i.e. anhydride, acid halide) or by using a coupling agent. In some cases, high temperatures (>200 °C) can overcome salt formation by driving off water, without the need for "activation" of the carboxyl group. The downside to this simple reation is that the compounds may decompose at these elevated temperatures. The carboxylic acid...
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