D' PAVIA

1
D. PAVIA CHEM 425a/552
Natural Products Chemistry
BLUE PROBLEM
orange ppt
2,4-DNP
ACHIRAL
A
H
Zn-Hg / HCl
C9H15NO
C9H17N
CrO3 H2SO4
1 CH3I, NaOH 2 Ag2O 3 heat
xs CH3OH
B
C
H
C9H15NO4
C11H19NO4
I
a diacid
C10H19N
1 CH3I, NaOH 2 Ag2O 3 heat
1 CH3I, NaOH 2 Ag2O 3 heat
1 CH3I, NaOH 2 Ag2O 3 heat
D
E
(CH3)3N
C12H21NO4
C10H14O4
J
(CH3)3N
1 O3 2 H3O
H3O
2 H2 Pt
mp 140o anilide 187o amide 216o
F
G
an acid
2
C8H10O4
C8H14O4
2
NOTES
1. Zn-Hg / HCl is the Clemmensen Reduction
(remember?).
2. The melting points which are given will have
to be looked up in a handbook of organic
compounds. The first mp is that of the
compound, the others are of derivatives which
will be appropriate for the type of compound
you have at that point.
3. Where derivatives are given, you should also
draw their structures as a part of your
answer.
4. 2,4-DNP is 2,4-dinitrophenylhydrazine
solution.