Summary of Reactions 777
g.Reaction of an amidewith lithium aluminum hydride forms an amine:
- Reactions of aldehydesand ketoneswith amines (Section 18.6).
a.Reaction with a primary amineforms an imine:
When the product is a Schiff base; Z can also be OH, or
b.Reaction with a secondary amineforms an enamine:
c.The Wolff–Kishner reduction converts a carbonyl group to a methylene group:
- Reactions of an aldehydeor a ketonewith oxygen nucleophiles.
a.Reaction of an aldehydeor a ketonewith water forms a hydrate (Section 18.7):
b.Reaction of an aldehydeor a ketonewith excess alcohol forms an acetal or a ketal (Section 18.8):
OH
OR′′
RRC ′ + H 2 O
OR′′
OR′′
+ 2 R′′OH RRC ′
HCl
O
C
R R′
OH
OH
+ H 2 O RRC ′
HCl
O
C
R R′
RRCH 2 ′
O
C
R R′
NH 2 NH 2
HO−,^ ∆
+ RNHR + H 2 O
CH
CO
R
CN
R R
C R
catalytic
H+
Z=R, NH 2 ,NHC 6 H 5 ,NHC 6 H 3 (NO 2 ) 2 , NHCONH 2.
catalytic
H+
+ H 2 NZ C NZ + H 2 O
R
R
C
R
R
O
RNRCH 2 ′
R′′
NR′
R′′
R
- LiAlH 4
2. H 2 O
R CH 2 NHR′
R NHR′
- LiAlH 4
2. H 2 O
RNHCH 2 2
NH 2
- LiAlH 4
2. H 2 O
O
C
O
C
R
O
C
