Problems for Chapter 1 & 2 ANSWERS

1. Draw an appropriate Lewis electron dot structure for the compound HONNH.
Valence electrons
2xH = 2
2xN = 10
O = 6
TOTAL = 18
H N N O H
2. Show the formal charge, if one exists, on each atom in the Lewis electron dot
structure at below:
HO
C
O
O
FC = 6-!/2(2) - 6 = -1
FC = 6-!/2(4) - 4 = O
FC = 4-!/2(8) - 0 = O
FC = 6-!/2(4) - 4 = )
3. Rewrite the structural formula, below, using a Kekule structure.
(CH
3
)
2
CHCH(CH
3
)CH=CHCH(OH)CH
3
C
CH
3
H
3
C
H
C
H
CH
3
C C
H H
C
H
O
CH
3
H
4. Show the three-dimensional structure for the compound, AlBr
3
. If the
compound has an overall dipole moment, show the direction of that dipole with
an arrow, +.
Br
Al
Br
Br
Trigonal Planar Shape
(flat, like a 3 bladed
propellar)
These two dipoles, have vectors which resolve into a
vector equal in magnitude to, but opposite direction to
the one pointing up...NO NET DIPOLE
5. Show the three-dimensional structure for the compound, NH
3
. If the compound
has an overall dipole moment, show the direction of that dipole with an arrow,
+.
H
N
H
H
NET DIPOLE
Pyramidal shape,
based on sp
3
nitrogen
6. Draw a Lewis dot structure for the following compounds, show formal charge
if any
a. CH
3
CH=O b. NH
4
+
N H H
H
H
C C O
H H
H
H
+1
7. Draw the Kekule structures for the above condensed structures.
H
C H
H
C
H
O
H
N H H
H
8. Draw the 3-D shape of each molecule, in question (6) above, about the
a. right carbon atom b. nitrogen
C O
H
CH
3
Trigonal Planar
H
N
H H
H
Tetrahedral
9. Name the 3-D shape of each molecule in question (6), about the:
a. right carbon atom b. nitrogen
Trigonal Planar Tetrahedral
10. Name the orbital hybridization for the compounds in question (6) above, about
the:
a. right carbon atom b. nitrogen
sp
2
sp
3
11. What will be the approximate bond angles in the molecules in question (6)
above, about the:
a. right carbon atom b. nitrogen
120 109
12. Carbon can exist in a trivalent state (three bonds) but neutral in charge. Predict
(show) the Lewis structure for such a carbon with all bonds to hydrogen.
H
C H
H
13. What orbital hybridization is likely for the carbon in the above species?
Remember that hybridized electrons are always paired (bonded or non-
bonded). Draw the carbon showing all orbitals.
H C
H
H
Carbon is sp
2
hybridized, with one p
orbital left for the unpaired electron
to reside in
14.Draw the Kekul structure for the skeletal drawing shown below.
C C
CH
3
CH
3
C C
H
H
H
H
H
H
CH
3
CH
3
H
C C
H
H
H
H
H
15.Draw the above compound in a condensed structure.
CH
3
CH
2
C[CH(CH
3
)
2
]C(CH
3
)
2
CH
2
CH
3
16. Show, with an arrow, the polar bonds and the direction of polarity in the
following molecules.

C C C C
O
CH
3
H
H
H
H
H
H
H
H
Cl

C C C C N
O H
H
H
H
H
H
H
H
H
17. What will be the numerical value of the K
a
whose pK
a
is 4.2?
(You may use two different powers of ten as your answer.)
pKa = - Log Ka,
pKa = 4.2
Ka = 10
-4.2
= 0.00063
18 If a compound is 62.041% carbon and 10.412% hydrogen, what is its empirical
formula?
If there is 62.031% carbon and 10.412% hydrogen, there must be 27.547% oxygen
in sample.
In 100 g of sample there is: 62.041 g C, 10.412 g H and 27.547 g O.
In 100 g of sample there is: 62.041g/12.011 = 5.16 moles of Carbon,
10.412g/1.008 = 10.33 moles of Hydrogen
27.547g/15.999 = 1.72 moles of Oxygen
Molar ratio :C
5.16
, H
10.33
, O
1.72,
divide all by smallest ratio i.e. 1.72, formula becomes
C
3
H
6
O
19. Identify the acids and bases in the following equation.
CH
3
CH
2
CH
2
CH
O
+ CH
3
CH
2
CH
2
CH
2

Li
+
CH
3
CH
2
CH
2
CH
3
CH
3
CH
2
CHCH
O
+
acid base conjugate base conjugate acid
20. The OH ion is the conjugate base of H
2
O. If water has a pKa of 15.7, which of
the following acids would be completely neutralized by NaOH? Circle them.
(Bold is correct answer)
Acid pKa
A 14
B 20
C 33
A-H +
-
OH A
-
+ H
2
O
B-H +
-
OH B
-
+ H
2
O
C-H +
-
OH C
-
+ H
2
O
pKa =14 pKa = 15.7
pKa = 15.7
pKa = 15.7
pKa =20
pKa =33
K
eq
K
eq
K
eq
K
eq
= 10
Pka(conj acid)
10
pKa (acid)
K
eq
= 10
1.7
K
eq
= 10
-4.3
K
eq
= 10
-17.3
21. Draw the following molecules in their three dimensional form and show, on the
structure, the following: (1) The polarity of each polar bond (>) and (2) The
overall polarity direction of the molecule (+>). If there is no molecular
dipole moment, circle the structure

CH
3
NH
2
BF
3
N
H
H
H
C
H
H
Net Dipole
B
F
F F
Dipole moments
Cancell
22. Compounds A and B, at right, have the same polar CN bond. However,
A has a dipole moment of 1.31 D while that of B is 2.11 D. Explain why B
has almost double the dipole moment of A. Illustrate your explination.
(Hint: Look at formal charges in structure B)
N
H
H
H
C
H
H
Net Dipole
N N N
H
C
H
H
Extremely large dipole
oriented toward negative charge
23. In each of the following chemical reactions, circle the acid and place an X
over the conjugate base.

CH
3
CH
2
OH + Na
+

CH
3
CH
3
CH
2
O

+
Na + CH
4
CH
3
CCH
2
CCH
3
+ NH
2

O O
CH
3
CCHCCH
3

+ NH
3
O O
AlCl
3
+ HCl AlCl
4

+ H
+
AlCl
3
+ NH
3
H
3
N
+

AlCl
3

X
X
X
Lewis Acid
24. Combustion analysis of an organic compound shows it to have 64.3% carbon
and 7.2% hydrogen. What is the emperical formula for the compound?
If there is 64.3% carbon and 7.2% hydrogen, there must be 28.5% oxygen in sample.
In 100 g of sample there is: 64.3 g C, 7.2 g H and 28.5 g O.
In 100 g of sample there is: 64.3g/12.011 = 5.35 moles of Carbon,
7.2g/1.008 = 7.14 moles of Hydrogen
28.5g/15.999 = 1.78 moles of Oxygen
Molar ratio :C
5.35
, H
7.14
, O
1.78,
divide all by smallest ratio i.e. 1.78, formula becomes C
3.00
H
4.01
O
C
3
H
4
O
25.Identify the Lewis acids and bases in the reactions of question (23).

CH
3
CH
2
OH + Na
+

CH
3
CH
3
CH
2
O

+
Na + CH
4
CH
3
CCH
2
CCH
3
+ NH
2

O O
CH
3
CCHCCH
3

+ NH
3
O O
AlCl
3
+ HCl AlCl
4

+ H
+
AlCl
3
+ NH
3
H
3
N
+

AlCl
3

Lewis Acid
Lewis acids are electron acceptors
Lewis Acid
Lewis Acid
Lewis Acid
Lewis bbases are electron donors
Lewis Base
Lewis Base
Lewis Base
Lewis Base
26.How can you explain the fact that the O-H bond in methanol(CH
3
-OH) is more
acidic than the C-H bonds.
Compare the conjugate bases which are formed when methanol (CH3-OH) acts
as an acid by breaking either the O-H or C-H bond:
H CH
3
O CH
3
O + H
+
Negative charge resides
on more electronegative
oxygen atom.
HOH
2
C H
HOH
2
C + H
+
Negative charge resides
on less electronegative
carbon atom.
The conjugate base with the negative charge on the oxygen is more stable