20.2 Outline a procedure for separating a mixture

H
N
O
A
H
N
H
N N
OH
N C N
20.51 Propose a mechanism that can explain occurrence of this reaction:
N
O
Answer:
N
O
COOH
COOH
N
O
+
H
O O O
N
O
COOH
O
O
N
O
O
H
C
COOH O O O
O
O
+
CH3
N
O
O
C
O
N
O
O O
O
O
H
TsCl
N
O
O
O
CH 3
H
N N
N
OTs
C
COOH
O
O O
20.52 When acetone is treated with anhydrous ammonia in the presence of anhydrous calcium
chloride (a common drying agent), crystalline product C is obtained on concentration of the
organic liquid phase of the reaction mixture.
These are spectral data for product C:
MS (m/z): 155 (M + ·), 140
IR (cm -1 ): 3350 (sharp), 2850-2960, 1705
1
H NMR (δ): 2.3 (s, 4H), 1.7 (1H; disappears in D2O), and 1.2 (s, 12H)
(a) What is the structure of C?
N
O
O
C
O
H
N
O
H
O