Organic Chemistry II Jasperse
1
Acid-Base Practice Problems
A. Rank the basicity of the following sets: Multiple Variable Problems
1. CH3MgBr
CH3NHNa
CH3NH2
(CH3)2NH
O
2.
3.
4.
O
O
CH3NH2
OH
ONa
NHNa
O
NH
ONa
OH
O
O
OH
O
T
5. CH3NHNa
CH3C(O)NH2
(CH3)3N
pyridine
6.
pyridine
CH3NH2
water
7. (CH3)3N
PhCO2Na
CH3NH2
PhCH2ONa
8. (CH3)3N
4-methylaniline
(CH3)3N
aniline
pyrrole
Aromaticity lost
Methyl donor makes more basic
9. methylamine
4-ethanoylaniline
aniline
pyridine
Carbonyl withdrawer makes less basic
10. CH3NH2
CH3CH2ONa
PhCO2Na
water
methanol
2
B. Rank the acidity of the following sets: Multiple Variable Problems
11.
OH
OH2
OH
HF
O
O
NH 3
OH
NH 2
12.
H 2O
O
OH
OH
NH 3
NH 2
O
13.
OH
OH
NH 3
H2
N
NH 3
H2
N
O
14.
NH 2
OH
15.
NH 2
H2
N
NH 3
O
16.
OH
OH
NH 3
OH
O
O
17.
OH
H 3O
18.
OH
O
OH
A
O
NH 2
19. For the following structures:
a. Which will extract from ether into neutral water?
b. Which will extract from ether into basic (NaOH) water?
c. Which will extract from ether into acid (HCl) water?
O
B
D
OH
OH
C
OH
O2N
NH 2
D