Ch 17

A functional group where a terminal carbon is part of a carbonyl group, >C=O, and is bound to a hydroxyl group, -OH, to form a carboxylic acid, RCOOH

A compound containing an acyl group, (R-C=O)- ; it is usually derived from a carboxylic acid, such as an ester, acyl halide, amide, or carboxylic acid anhydride.

Molecule containing a carbonyl group, >C=O , that is attached to a hydroxyl group, -OH , which is called a carboxyl group, -COOH, with the general formula RCOOH.

 Compound that yields a carboxylic acid on hydrolysis, such as esters, acid anhydrides, acyl chlorides, amides, and nitriles

The anion resulting from deprotonation of a carboxylic acid, RCOO‾ ; it is isolated as the salt of the carboxylic acid.

Compound with two carboxyl groups, -COOH. Also called alkanedioic acid

A molecule containing a carbonyl group, >C=O , that is attached to an alcohol group, -OR' , with the general formula RCOOR' , often formed by the reaction of a carboxylic acid and an alcohol with loss of water. Also called carboxylic ester.

An activated carboxylic acid derivative formed from two acid molecules with loss of a molecule of water; a mixed anhydride is derived from two different carboxylic acid molecules

An activated carboxylic acid derivative in which the hydroxyl group of the acid is replaced by a chlorine atom, RCOCl

A molecule containing a carbonyl group, >C=O , that is attached to an amino group, -NR2 , with the general formula RCONR'2 (R may be hydrogen); often formed by the reaction of a carboxylic acid and an amine, with loss of water

A molecule containing a cyano group, -C≡N , with the general formula RCN

 A compound with a hydroxyl group and a cyano group on the same carbon atom, R2C(OH)(CN), derived by adding HCN to an aldehyde or ketone

A reaction in which a carboxylic acid group is introduced in a substrate, such as the addition of CO2 to a Grignard reagent: RMgX + CO2 → RCOOH. Also called carbonation.

Two-stage substitution reaction, in which one type of carboxylic acid derivative is converted into another, which involves addition and elimination reactions; in the addition stage, the nucleophile adds to the carbon that bears the leaving group; in the elimination stage, the leaving group is expelled

Two-stage mechanism for a nucleophilic addition-elimination reaction; in the addition stage, the nucleophile adds to the carbon that bears the leaving group, then in the elimination stage, the leaving group is expelled

The substituent that departs with a lone pair of electrons from the substrate in a nucleophilic substitution reaction. The best leaving groups depart as stable weak bases.

The acid-catalyzed reaction of a carboxylic acid with an alcohol to give a carboxylic ester and water

Substitution of one alkoxy group for another in an ester, which can take place under either acidic or basic conditions

Basic hydrolysis of an ester into an alcohol and a carboxylate salt

A cyclic ester; δ-hydroxyacids can undergo an intramolecular esterification to produce δ-lactones, which contain a six-membered ring

A compound with two carbonyl groups bound to the same nitrogen atom, RCONHCOR'

A cyclic amide; δ-aminoacid can undergo an intramolecular condensation to produce δ-lactams, which contain a six-membered ring

The inorganic, weak diprotic acid, HOC(=O)OH, or H2CO3 ; its acid dissociation constants are pKa1 = 6.35 and pKa2 = 10.2 ; it is formed by the equilibrium reaction between water and carbon dioxide: H2O + CO2 ↔ H2CO3

The simplest acid chloride, ClCOCl , that is formally derived from carbonic acid. Also called phosgene

 A diester of carbonic acid, ROC(=O)OR'

An amide of carbonic acid, HOC(=O)NH2

An ester, ROC(=O)NHR', that is formed by the reaction between an alkyl chloroformate, ROC(=O)Cl, and an amine, R'NH2 ; it can also be formed by the reaction between an alcohol, ROH, and an isocyanate, R'-N=C=O ; carbamate derivatives formed by reacting an alcohol with α-naphthyl isocyanate are crystalline solids with sharp melting points. Also called urethane

An organic compound that is the diamide of carbonic acid, H2NCONH2 , with two amine groups, -NH2 , joined to a carbonyl group, >C=O . Also called carbamide

(1) A chemical reaction that releases carbon dioxide. (2) A reaction whereby a carboxylic acid, RCOOH, loses a carboxyl group, -COOH, as carbon dioxide, O=C=O.