15.18: Organic Acids and Bases and Some of Their Derivatives (Summary)
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To ensure that you understand the material in this chapter, you should review the meanings of the following bold terms in the summary and ask yourself how they relate to the topics in the chapter.
A carboxylic acid (RCOOH) contains the functional group COOH, called the carboxyl group, which has an OH group attached to a carbonyl carbon atom. An ester (RCOOR′) has an OR′ group attached to a carbonyl carbon atom. An amine is derived from ammonia (NH3), with one, two, or all three of the hydrogen atoms of NH3 replaced by an alkyl (or an aryl) group. The amide functional group has a carbonyl group joined to a nitrogen atom from NH3 or an amine.
There are many familiar carboxylic acids. The R group may be a hydrogen atom (as in formic acid, HCOOH), an alkyl group (as in acetic acid, CH2COOH), or an aryl group (as in benzoic acid, C6H5COOH). The location of substituents along the carbon chain is indicated by a Greek letter (for common names) or a number (for names from the International Union of Pure and Applied Chemistry).
A carboxylic acid is formed by the oxidation of an aldehyde with the same number of carbon atoms. Because aldehydes are formed from primary alcohols, these alcohols are also a starting material for carboxylic acids.
Carboxylic acids have strong, often disagreeable, odors. They are highly polar molecules and readily engage in hydrogen bonding, so they have relatively high boiling points.
Carboxylic acids are weak acids. They react with bases to form salts and with carbonates and bicarbonates to form carbon dioxide gas and the salt of the acid.
Esters are pleasant-smelling compounds that are responsible for the fragrances of flowers and fruits. They have lower boiling points than comparable carboxylic acids because, even though ester molecules are somewhat polar, they cannot engage in hydrogen bonding. However, with water, esters can engage in hydrogen bonding; consequently, the low molar mass esters are soluble in water. Esters can be synthesized by esterification, in which a carboxylic acid and an alcohol are combined under acidic conditions. Esters are neutral compounds that undergo hydrolysis, a reaction with water. Under acidic conditions, hydrolysis is essentially the reverse of esterification. When carried out under basic conditions, the process is called saponification.
Inorganic acids also react with alcohols to form esters. Some of the most important esters in biochemistry are those formed from phosphoric acid.
Amines are nitrogen-containing organic molecules derived from ammonia (NH3). A primary (1°) amine (RNH2) has one organic group bonded to the nitrogen atom, a secondary (2°) amine (R2NH) has two organic groups bonded to the nitrogen atom, and a tertiary (3°) amine (R3N) has three organic groups bonded to the nitrogen atom. Amines are basic compounds that react with strong acids to produce ammonium (NH4+) salts. A cyclic compound in which the ring contains one or more noncarbon atoms is called a heterocyclic compound. There are many heterocyclic amines, including many physiologically important ones. Alkaloids are heterocyclic amines found in many plants. Caffeine, nicotine, and cocaine are familiar alkaloids.
Organic compounds containing a carbonyl group bonded to a nitrogen atom are amides, and the carbon-to-nitrogen bond is an amide linkage (or a peptide linkage). Most amides are colorless and odorless, and the lighter ones are soluble in water. Because they are polar molecules, amides have comparatively high boiling points and melting points. Amides are synthesized from carboxylic acids and NH3 or amines. Amides are neutral compounds. They resist hydrolysis in water, but acids, bases, and enzymes catalyze the reaction.