525 / 912
Chapter 16 517
Copyright © 2017 Pearson Education, Inc.
hydrazone
R
(H)R
C N NH
2
imine (Schiff base)
C N R
(H)R
R
ketone
R R
C
O
nucleophilic addition–elimination reaction
a reaction involving nucleophilic addition to a carbonyl group to form a tetrahedral
intermediate, which then undergoes elimination of a leaving group. Imine forma-
tion is an example: an amine adds to the carbonyl carbon, and water is eliminated.
nucleophilic addition
reaction
a reaction that involves the addition of a nucleophile to the carbonyl carbon of an
aldehyde or a ketone.
oxime
C N OH
(H)R
R
pH-rate profile
a plot of the rate constant of a reaction versus the pH of the reaction mixture.
phenylhydrazone
C N NHC
6
H
5
(H)R
R
protecting group
a group that protects a functional group from a synthetic operation that it would
otherwise not survive.
reduction reaction
in the case of an organic molecule, a reaction in which the number of
C
¬
H
bonds
is increased or the number of
C
¬
O, C
¬
N,
or
C
¬
X
(X
=
halogen) bonds is
decreased.
reductive amination
a reaction of an aldehyde or a ketone with ammonia or with a primary amine in the
presence of a reducing agent.
synthetic equivalent
the reagent actually used as the source of a synthon.
synthon
a fragment of a disconnection.
Wittig reaction
a reaction of an aldehyde or a ketone with a phosphonium ylide, resulting in the
formation of an alkene.
ylide
a compound with opposite charges on adjacent covalently bonded atoms with
complete octets.