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Chapter 15 483
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symmetrical anhydride
an acid anhydride with identical R groups.
tetrahedral intermediate
the intermediate formed in an adddition–elimination (or a nucleophilic acyl
substitution) reaction.
thioester
the sulfur analog of an ester.
O
C
R SR
transesterification reaction
the reaction of an ester with an alcohol to form a different ester.
carboxylic acid derivative
a compound that is hydrolyzed to a carboxylic acid.
carboxyl oxygen
the single-bonded oxygen of a carboxylic acid or ester.
catalyst
a species that increases the rate of a reaction without being consumed or
changed in the reaction.
ester
O
C
R OR
Fischer esterification
a reaction of a carboxylic acid with excess alcohol and an acid catalyst.
reaction
Gabriel synthesis
a method used to convert an alkyl halide into a primary amine, involving S
N
2
attack of phthalimide ion on an alkyl halide followed by hydrolysis.
hydrolysis
a reaction with water that converts one compound into two compounds.
imide
a compound with two acyl groups bonded to a nitrogen.
lactam
a cyclic amide.
lactone
a cyclic ester.
mixed anhydride
an acid anhydride with two different R groups.
nitrile
a compound that contains a carbon–nitrogen triple bond.
R C N
nucleophilic acyl
substitution reaction
a reaction in which a group bonded to an acyl group is substituted by another group.
nucleophilic addition–
elimination reaction
another name for a nucleophilic acyl substitution reaction, which emphasizes the
two-step nature of the reaction: a nucleophile adds to the carbonyl carbon in the
first step, and a group is eliminated in the second step.