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Solutions for Ketones and Aldehydes
35 Imines can be formed in either acid or base conditions. Here, the hydrazone formation is shown in 
acid conditions.
O
N
NH2NH2
H2O
H2O
NHNH2
O H
N
H
NH2
N
NH2
HC
O
NHNH2
H H
− H2O
O
H C
O
H
H
NHNH2
O H
H3O+
NH2
A
B
C
DE
F
N
N HH
OH
NH
N
H
H
H OH
C
N
NH
C
H
N N
H
N
N
H OH
NH
N
H
reduction of the hydrazone
+
N2 is nature's best leaving group: 
it is very stable, and a gas, so it 
bubbles out of the reaction mixture.
H H H H OO
H H HH
H H(d)(c)(b)(a)
36
Follow the six steps A–F of imine formation in the solution to 21(a).
OH
H A
Aqueous acid first 
hydrolyzes the acetal; 
the Zn(Hg)/HCl then 
reduces both ketones.
common name:
indane
433