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Chapter 18
Carboxylic Acids & Their Derivatives
24
Chemistry
Undergraduate 4
05/02/2011

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Term
Carboxyl group
Definition
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
Term
Carboxylic acid
Definition
A molecule containing a carbonyl group, >C=O , that is attached to a hydroxyl group, -OH, with the general formula: RCOOH
Term
Carboxylic acid derivative
Definition
Compound that yields a carboxylic acid on hydrolysis, such as esters, acid anhydrides, acyl chlorides, amides, and nitriles
Term
Carboxylate ion
Definition
The anion resulting from deprotonation of a carboxylic acid, RCOO‾ ; it is isolated as the salt of the carboxylic acid
Term
Dicarboxylic acid
Definition
Compound with two carboxyl groups, -COOH. Also called alkanedioic acid
Term
Ester
Definition
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
Term
Carboxylic acid anhydride
Definition
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. Also called carboxylic anhydride, or acid anhydride
Term
Acyl chloride
Definition
An activated carboxylic acid derivative in which the hydroxyl group of the acid is replaced by a chlorine atom, RCOCl. Also called acid chloride.
Term
Amide
Definition
A molecule containing a carbonyl group, >C=O , that is attached to an amino group, -NR2 , with the general formula RCONR2' (R may be hydrogen); often formed by the reaction of a carboxylic acid and an amine, with loss of water
Term
Nitrile
Definition
A molecule containing a cyano group, -C≡N , with the general formula RCN
Term
Cyanohydrin
Definition
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
Term
Carboxylation
Definition
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
Term
Nucleophilic acyl substitution
Definition
Two-stage substitution reaction in which one type of carboxylic acid derivative is converted into another Also called an acyl transfer reaction, or a nucleophilic addition- elimination reaction
Term
Addition-elimination mechanism
Definition
Two-stage mechanism for nucleophilic acyl substitution reactions and nucleophilic aromatic substitution (SNAr) reactions; 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
Term
Fischer esterification
Definition
The acid-catalyzed reaction of a carboxylic acid with an alcohol to give a carboxylic ester and water
Term
Transesterification
Definition
Substitution of one alkoxy group for another in an ester, which can take place under either acidic or basic conditions
Term
Saponification
Definition
Basic hydrolysis of an ester into an alcohol and a carboxylate salt
Term
Lactone
Definition
A cyclic ester
Term
Imide
Definition
A compound with two carbonyl groups bound to the same nitrogen atom, RCONHCOR'
Term
Lactam
Definition
A cyclic amide
Term
Carbonic acid
Definition
The inorganic, one-carbon dicarboxylic acid, HOCOOH, or H2CO3
Term
Carbonate ester
Definition
A diester of carbonic acid, ROCOOR
Term
Urea
Definition
A diamide of carbonic acid, H2NCONH2
Term
Decarboxylation
Definition
A reaction whereby a carboxylic acid loses a carboxyl group as carbon dioxide, CO2
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