chapter 21 - carboxylic acid derivatives

acid derivatives

compounds containing functional group that can be converted to carboxylic acids by acidic or basic hydrolysis

acid halide

an activated acid derivative in which the hydroxy group of the acid is replaced by a halogen, usually chlorine

acyl transfer

another term for a nucleophilic acyl substitution. emphasizes the transfer of the acyl group from the leaving group to the attacking nucleophile

amide

an acid derivative in which the hydroxy group of the aid is replaced by a nitrogen atom and its attache hydrogens or alkyl groups. is a composite of a carboxylic acid and an amine

ammonolysis of an ester

cleavage of an ester by ammonia or an amine to give an amide and an alcohol

anhydride

an activated acid derivative formed form 2 acid molecules with loss of a molecule of water

mixed anhydride

an anhydride derived from 2 different acid molecules

carbonate ester

a dieter of carbonic acid

carbonic acid

the one-carbon dicarboxylic acid, HOCOOH. carbonic acid is constantly in equilibrium with carbon dioxide and water. its esters and amides are stable, however.

ester

an acid derivative in which the hydroxy group of the acid is replaced by an alkoxy group. an ester is a composite of a carboxylic acid an an alcohol

Fischer esterification

combining a carboxylic acid and an alcohol under acidic conditions to give an ester

isocyanate

a compound of formula R-N=C=O

lactam

a cyclic amide

lactone

a cyclic ester

nitrile

an organic compound containing the cyan group

nucleophilic acyl substitution

a nucleophile substitutes for a leaving group on a carbonyl carbon atom. nucleophilic acyl substitution usually takes place through the addition-elimination mechanism

polymer

a large molecule composed of many smaller units (monomers) bonded together

polyamide

(nylon) a polymer in which the monomer units are bonded by amide linkages

polycarbonate

a polymer in which the monomer units are bonded together by carbonate ester linkages

polyester

a polymer in which the monomer units are bonded by ester linkages

polyurethane

a polymer in which the monomer units are bonded together by carbamate ester (urethane) linkages

saponification

basic hydrolysis of an ester to an alcohol and a carboxylate salt

thiester

an acid derivative in which the hydroxy group of the acid is replaced by a sulfur atom an dits attached alkyl or aryl group. a thirster is a composite of a carboxylic acid and a thiol

transesterification

substation of one alkoxy group for another in an ester transesterification can take place under either acidic or basic conditions

triglyceride

(triacylglycerol) a trimester of the trial glycerol, esterified with 3 fatty acids

urea

a diamine of carbonic acid

urethane

(carbamate ester) an ester of a carbonic acid, RNH—COOH; a monster, monoxide of a carbonic acid