Solutions to Practice Problems #1
Summer 2017
Chem 2401
Page 1 of 2
Solutions to Practice Problems #1
1. Arrange the species in each of the following sets in order of increasing
acidity.
1 = least acidic, 4 = most acidic
a)
b)
3
1
2
4
CH3CH2OH, CH3CH2CH3, CH3CH2NH2, CH3CH2SH
O-based
C-based
S-based
N-based
3
1
2
CH3OCH3, CH3OCH3, CH3NHCH3
C-based
N-based
H
O-based,
charged
2 CH3
c)
1
3H
CH3NCH3, CH3CH2CH3, CH3OCH3
C-based
H
O-based,
N-based,
charged
charged
2. Arrange the species in each of the following in order of decreasing
basicity.
1 = most basic, 3 = least basic
1
CH3NHCH3,
lone pair on N
a)
2
NH2,
lone pair on N,
neg. charge
b)
1
CH3NCH3,
lone pair on N,
neg. charge
c)
2
3
CH3CH2CH3 , CH3OCH3
no lone pairlone pair on O
NOT A BASE!
1
CH3,
lone pair on C,
neg. charge
2
CH3O,
lone pair on O,
neg. charge
4
F,
lone pair on F,
neg. charge
3 O
CH3CO
lone pair on O,
neg. charge,
but delocalized
3
OH
lone pair on O,
neg. charge
Solutions to Practice Problems #1
Summer 2017
Chem 2401
Page 2 of 2
3. In the following equations, reactants and arrows showing the flow of
electrons are indicated. Supply the products of the reactions. Careful with
charges!
+
a)
H
H
N H
N H
H
H
CH3
CH3
CH3CHO
+
H O
CH3CHOH
I CH2
CH3NH CH2
O
+
b)
CH3NH
+
I
+
c)
+
+
H
H Cl
Cl
d)
4. For the following reactions, complete the Lewis structures for the pertinent
parts of the molecules and draw curved arrows to show the electronic
changes taking place.
CH2
CH2 F
F
+
a)
O
O
Cl
C
+
Cl
CH3OH
C
CH3OH
b)
H
6 5 4 3
6 O
1 2
OH
1
2
5
4
3
c)
N
N
+
d)
CH3
I
CH3
+
I