Problems 667- When heated with an acidic solution of sodium dichromate, compound A forms benzoic acid. Identify compound A from its
NMR spectrum. - Describe two synthetic routes for the preparation of p-methoxyaniline with benzene as the starting material.
- Which is a more stable intermediate?
a. b.- If phenol is allowed to sit in that contains a small amount of what products would be formed?
- Show how the following compounds could be prepared from benzene:
a. b. c.- An unknown compound reacts with ethyl chloride and aluminum trichloride to form a compound that has the following NMR
spectrum. Give the structure of the compound.
10 9 8765 4 3 210
δ (ppm)
frequency(^1) H
CH 3 C
O
SO 3 H
CH 2 CH(CH 3 ) 2
OCH 3
Br
NO 2
CH 3
CH 3 CCH 2
D 2 O D 2 SO 4 ,
−
NO 2
Cl
Cl
HO
−
NO 2
OH
- or
OH
H NO 2 H NO 2
CH 3
or
87654 3210
(ppm)
frequency
1.3 1.2 1.1PPM
(^1) H