When a carboxylic acid group is connected to a ring, the compound is named as In the previous section, we learned about the reaction between a carboxylic
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Carboxylic Acids &
Their Derivatives
Organic Chemistry, 2nd Edition
David R. Klein
Introduction to Carboxylic Acids
Carboxylic acids are compounds with a -COOH group. These compounds are abundant in nature, where they are responsible for some familiar odors. Carboxylic acids are also found in a wide range of pharmaceuticals that are used to treat a variety of conditions.Nomenclature of Carboxylic Acids
Monocarboxylic Acids
Monocarboxylic acids, compounds containing one carboxylic acid group, are named with the suffidž ͞oic acid"͗ The parent is the longest chain that includes the carbon atom of the carboxylic acid group. That carbon atom is always assigned number 1 when numbering the parent. When a carboxylic acid group is connected to a ring, the compound is named as an alkane carboxylic acid; for example: Many simple carboxylic acids have common names accepted by IUPAC.Diacids
Diacids, compounds containing two carboxylic acid groups, are named with the suffix͞dioic acid"; for example:
Many diacids have common names accepted
by IUPAC.Structure and Properties of Carboxylic Acid
The carbon atom of a carboxylic acid group is sp2
hybridized and therefore exhibits trigonal planar geometry with bond angles that are nearly 120°Carboxylic acids can form two hydrogen-bonding
interactions, allowing molecules to associate with each other in pairs.Acidity of Carboxylic Acids
Carboxylate salts are ionic and are therefore more water-soluble than their corresponding carboxylic acids. Carboxylate ions are named by replacing the suffidž ͞ic acid" with ͞ate"; for edžample͗ When dissolved in water, an equilibrium is established in which the carboxylic acid and the carboxylate ion are both present. In most cases, the equilibrium significantly favors the carboxylic acid with a Ka usually around 10-4 or 10-5. In other words, the pKa of most carboxylic acids is between 4 and 5.Carboxylic Acids at Physiological pH
Our blood is buffered to a pH of approximately 7.3, a value referred to as physiological pH. When dealing with buffered solutions, you may recall the Henderson-Hasselbalch equation. When the pKa value of an acid is equivalent to the pH of a buffered solution into which it is dissolved, thenThe ratio of the concentrations of conjugate base and acid will be 1. In other words, a carboxylic acid and its conjugate base will be present in approximately equal amounts when dissolved in a solution that is buffered such that pH = pKa of the acid. Now let's apply this equation to carboxylic acids at physiological pH (7.3), so that we can determine which form predominates (the carboxylic acid or the carboxylate ion). Recall that carboxylic acids generally have a pKa value between 4 and 5. Therefore, at physiological pH: The ratio of the concentrations of the carboxylate ion and the carboxylic acid will be approximately 1000 : 1. That is, carboxylic acids will exist primarily as carboxylate salts at physiological pH. For example, pyruvic acid exists primarily as pyruvate ion at physiological pH.Substituent Effects on Acidity
Preparation of Carboxylic Acids
Hydrolysis of Nitriles
Carboxylation of Grignard Reagents
Reactions of Carboxylic Acids
Under such conditions, the aldehyde cannot be isolated. Instead, it is further attacked by LAH to form an alkoxide, which is then protonated when H3O+ is introduced into the reaction flask. An alternative method for reducing carboxylic acids involves the use of borane (BH3).Selectivity
Introduction to Carboxylic Acid Derivatives
Classes of Carboxylic Acid Derivatives
In the previous section, we learned about the reaction between a carboxylic acid and LAH. This reaction is a reduction, because the carbon atom of the carboxylic acid group is reduced in the process: Carboxylic acids also undergo many other reactions that do not involve a change in oxidation state:Carboxylic Acid Derivatives in Nature
Naming Acid Halides
Acid halides are named as deriǀatiǀes of carbodžylic acids by replacing the suffidž ͞ic acid"
with ͞yl halide"͗ When an acid halide group is connected to a ring, the suffidž ͞carbodžylic acid" is replaced