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Carboxylic Acid

Definition

A carboxylic acid contains a carboxy (carboxyl) group, COOH, which has one oxygen atom doubly bonded to the carbon atom and a hydroxy (OH) group singly bonded to the carbon atom. The carbon atom of the carboxy group must also be attached to an organic group or a hydrogen. Examples of common carboxylic acids include:



Carboxylic acids that have long (12 to 24 carbon atom) unbranched aliphatic groups are called fatty acids.

Additional Info

The hydrogen atom of the carboxyl group can dissociate (detach as H⁺) only to a very small extent, behavior that classifies carboxylic acids as weak acids. For example, we can say that the following equilibrium lies very far to the left side of the reaction (i.e. very little acetate anion forms in solution):



The names of carboxylic acids should end in "oic acid" according to official IUPAC nomenclature rules (see link below), however older common names that end in "ic acid" are still used. The "oic acid" naming scheme is superior because it unambiguously identifies the material as a carboxylic acid. In cases where another functional group takes naming precedence, "carboxy" is used as a prefix, although in certain cases the suffix "carboxylic acid" may also be used!



When a carboxylic acid is neutralized with a base it becomes a salt that is itself a weak base. The salt is named using the suffix "oate" instead of "oic acid". Sodium benzoate, shown below, is a common food preservative:



Carboxylic acids occur naturally in many organisms, and are primary components of your DNA. Examples of carboxylic acids you routinely encounter include ascorbic acid (vitamin C), acetic acid (vinegar is a 5% aqueous solution of vinegar), and citric acid (responsible for the sourness/tartness of citrus fruits).

MSDS Relevance Carboxylic acids are generally weak acids, but that does not mean that they can not be corrosive or pose other hazards. Always use proper personal protective equipment (PPE) such as goggles and gloves when working with carboxylic acids. Take care to avoid storage or use with incompatible chemicals such as bases. Avoid storing containers in metal cabinets, which can corrode. Caroxylic acids may also be flammable or combustible. Further Reading William Reusch has a great discussion of carboxylic acids. Steve Glover's tutorial on carboxylic acids. See the University of Maine for more info about carboxylic acids. IUPAC nomenclature rules for the naming of carboxylic acids. Carboxylic acids and Esters at the U of Akron. Study Organic Chemistry explains how to study and understand organic chemistry.

Keep your employees safe around acids with signs, spill trays and plastic storage cabinets from Safety Emporium.

See also: acid, corrosive, ketone, pH.

Additional definitions from Google and OneLook.

Disclaimer: The information contained herein is believed to be true and accurate, however ILPI makes no guarantees concerning the veracity of any statement. Use of any information on this page is at the reader's own risk. ILPI strongly encourages the reader to consult the appropriate local, state and federal agencies concerning the matters discussed herein.