1. In which one of the following are the three bonds listed in order of increasing polarity?

a. C–C < C=C < C≡C

b. C–Cl < C–Br < C–I
c. F–N < F–O < F–F
d. N≡N < O=O < F–F
e. Si–N < Si–O < Si–F

2. Which one of the following is the best Lewis structure for NO– ?
a. b. c. d. e.
N O N O N O N O N O

3. The table below lists the formal charges on the O atoms in water, hydronium cation, hydroxide
anion, and hydrogen peroxide. In which one of the rows a-e are all of the formal charges listed
correctly?
Formal Charge on O atoms
H2O H3O+ OH– H2O2
a. 0 0 0 0
b. 0 +1 –1 0
c. –½ –⅓ –1 –1
d. –2 –2 –2 –1
e. –2 –3 –1 –1

4. Which one of the following statements is true?

a. A nonpolar molecule can only have nonpolar bonds
b. All stable compounds of carbon are an exception to the octet rule.
c. The lone pair in a seesaw molecule structure is located in an axial position.
d. Magnesium metal combines with a non-metal such as chlorine by sharing two electrons.
e. The Lewis bonding model includes the concept of resonance structures because the electron
distribution in some molecules cannot be properly modeled using localized pairs of electrons.

5. Select the pair of oxyanions that have the same molecular shape:
a. PO33− and CO 32 − d. SO 32 − and CO 32 −
b. PO33− and NO3− e. SO 32 − and NO3−
c. PO33− and SO 32 −
6. For which of the following molecule(s) is the electron-group geometry the same as the
molecular geometry: SF4, SiF4, XeF4
a. Only SF4
b. Only SiF4
c. Only SF4 and XeF4
d. All of SF4, SiF4, and XeF4
e. None of SF4, SiF4, and XeF4

7. Which of the following molecules has(have) a non-zero dipole moment: SF4, SiF4, XeF4
a. Only SF4
b. Only SiF4
c. Only SF4 and XeF4
d. All of SF4, SiF4, and XeF4
e. None of SF4, SiF4, and XeF4

8. Arrange the following four σ-bonds in order of increasing average bond length:
C–Cl, Si–C, Si–Cl, Si–Si
a. C–Cl < Si–C < Si–Cl < Si–Si
b. C–Cl < Si–C < Si–Si < Si–Cl
c. Si–C < C–Cl < Si–Si < Si–Cl
d. Si–C < C–Cl < Si–Cl < Si–Si
e. Si–Si < Si–C < Si–Cl < C–Cl

9. In which of the following pairs of molecules does the central atoms have same hybridization?
a. BCl3, HNO c. CO2, O3 e. HOCl, ClF3
b. BeH2, NH3 d. H2O, H2CO

10. Which one of the following statements is true:

a. Energy is released when bonds are formed.
b. The electrons involved in the formation of a bond are always shared equally.
c. The distance between two bonded atoms, the bond length, is always constant.
d. A bond between two atoms is formed when the nucleus of one atom is attracted to the
nucleus of the other atom.
e. A bond between two atoms is formed when the electrons of one atom are attracted to the
electrons of the other atom.
11. Draw the best Lewis structure for the carbonate anion, CO 32 − . Which one of the following
statements best describes the real life molecular structure and charge distribution of
carbonate:
a. Carbonate has three C=O double bonds, with the –2 charge on the C atom.
b. Carbonate has three single C–O bonds, with a –1 charge on each O atom, and a lone pair
on the C atom.
c. Carbonate has three single C–O bonds, with a –1 charge on each O atom, and a +1 charge
on the C atom.
d. Carbonate has two C–O single bonds, with a –1 charge on each of these O atoms, and one
C=O double bond.
e. Carbonate has three equivalent C–O bonds, each of which is between a single and a
double bond, and the –2 charge is equally spread over the three O atoms.

12. The carbon-carbon sigma bonds in H2CCCH2 result from the overlap of:
a. sp hybrid orbitals with sp2 hybrid orbitals
b. sp hybrid orbitals with sp3 hybrid orbitals
c. sp2 hybrid orbitals with sp2 hybrid orbitals
d. unhybridized 2p atomic orbitals with unhybridized 2p atomic orbitals
e. unhybridized 2s atomic orbitals with unhybridized 2s atomic orbitals

13. Which one of the following statements is incorrect:

a. An sp3 hybrid orbital has 2 lobes of unequal size.
b. Pi bonds are generally stronger than sigma bonds.
c. The three carbon sp2 hybrid orbitals have the same energy.
d. Rotation about a pi bond requires the breaking of the pi bond.
e. The number of sp hybrid orbitals on the carbon atom in CO 32 − is zero.

14. What is the hybridization on the Br atom in BrO−2 , BrO3− , and BrO−4 ?
a. sp3 in all three anions
b. sp2 in BrO−2 and BrO3− , and sp3 in BrO−4
c. sp in BrO−2 , sp2 in BrO3− , and sp3 in BrO−4
d. sp2 in BrO−2 , and sp3 in both BrO3− and in BrO−4
e. None of the above are correct since any central atom that has an expanded octet must also
include d-atomic orbitals in the hybridization.
15. Based on molecular orbital theory, the bond orders of the Li-Li bonds in Li2, Li+2 , and Li2−
are:
Li2 Li+2 Li−2
a. 1 0 0
b. 1 0 ½
c. 1 ½ ½
d. 1 ½ 0
e. 1 ½ -½

16. According to band theory, why is a material such as diamond an insulator?

a. The bonds in diamond are too strong to allow atoms to move so no current flows.
b. There are no electrons in the valence band of diamond, thus no electrons to promote to
the conduction band.
c. Diamond has a very large energy gap between the valence band and the conduction band, and
under normal conditions very few electrons can make the transition between the bands.
d. All carbon atoms in diamond have a full octet of electrons, so there are no positive or
negative holes in the material.
e. Since all of the carbon atoms in diamond are covalently bonded, all of the electrons in
diamond are localized in pi bonds.

17. Which of the following could act as a p-type semiconductor?

a. tin with traces of lead
b. silicon with traces of boron
c. beryllium with traces of barium
d. germanium with traces of arsenic
e. aluminum with traces of scandium

18. Which of the following best represents the valence electron configuration of a C atom in the
simplest alkyne, acetylene (C2H2; energy increases from bottom to top).
a. p ↑ ↑ b. p ↑ ↑ ↑- c. sp3 ↑ ↑ ↑ ↑

sp ↑ ↑ sp ↑-
d. sp ↑ ↓
e. sp2 ↑ ↑ ↑ p ↓
p ↑ ↓
Question 19:
Draw the best Lewis structures for the following three molecular species. Where applicable,
draw all equivalent resonance structures.

CH2CHCN

FCO −2

IOF3 (central atom: I)

Question 20:
Draw a reasonable representation of the molecular geometry for fluoroethyne, FCCH; you do not
have to show any lone pairs. Show the direction of its molecular dipole moment using a molecular
dipole arrow: or dipole notation. Do not include bond dipole moment arrows.
Question 21:
a. The bonding framework for dinitrogen
pentoxide is provide is provided below.
• Provide the best Lewis structure by
drawing in any missing multiple bonds
and lone pairs.
• If applicable, indicate how many possible
equivalent resonance structures can be
drawn for this molecule.
b. It has been determined experimentally that
the N-O bond lengths in dinitrogen
pentoxide have two values: 118 pm and
136 pm. Indicate which N-O bond(s) are
118 pm and which N-O bond(s) are 136
pm in the bonding framework below. You
do not need to provide the Lewis structure
again.

O O O O O O
N N N N

O O O O

# equivalent resonance structures: ________

Question 22:
Draw the best Lewis structures for AsCl3, BrCl5, and GeCl2; all three molecules have a single
central atom. After completing the Lewis structures, fill in the table below.
AsCl3 BrCl5 GeCl2

List the value(s)

What is the name What is the name Is the molecule
of the ideal
Molecule of the electron of the molecular polar or nonpolar?
(VSEPR) bond
group geometry? geometry? Circle one.
angles.

AsCl3 polar / nonpolar

BrCl5 polar / nonpolar

GeCl2 polar / nonpolar

Question 23:
Methyl cyanoacrylate, C5H5O2N, is the active ingredient in superglue. Below is a picture of
methyl cyanoacrylate showing only the σ-bonds. C, N, and O atoms are labelled 1 – 8.
a. Complete the picture by drawing in b. Using the numbered labels (1 – 8), indicate
all π bonds and lone pairs using which atoms have the following hybridizations:
Lewis notation (dots and lines). sp sp2 sp3

c. Provide the ideal bond angle predicted by

VSEPR theory for the following angles:
N1-C2-C3 C2-C3-C4 C3-C5-O6 C5-O7-C8

Question 24:
The band gap for a semiconductor gallium arsenide, GaAs, is 138 kJ/mol. What is the longest
wavelength of electromagnetic radiation (in nm) that will induce a current in this material?

Answer: ____________ nm
Question 25:
Oseltamivir (Tamiflu, pictured below multiple times), is an antiviral drug used to fight influenza.
It is one of the first marketed drugs whose discovery was aided using computational chemistry.

A. In the picture below, circle all sp2 hybridized C atoms

O
H2 H H2
H
C O C C C
H
H 3C C C C O CH3
H
CH2 C CH2
H 3C HN C
H
C NH2
H 3C O

B. List the ideal (VSEPR) angle values about the central atoms
that have been labelled with dashed circles in the figure below. Ideal (VSEPR) angle
O
H2 a H H H2 H
H
C O C d C e C f H a. d.
H 3C C C C O C
H
CH2 C CH2 H b. e.
H 3C HN C
b c H
C N c. f.
H 3C O H H
Question 26:
The gas-phase molecule Al2 was studied using accurate quantum mechanics calculations. It was
found that Al2 is paramagnetic in its most stable form.
The 3s and 3p atomic orbitals can overlap in a similar manner as the 2s and 2p atomic orbitals to
give an analogous set of eight molecular orbitals. The energy ordering between the σ3p and π3p
molecular orbitals can be different for different species. Both possible molecular orbital diagrams
are provided below.
a. Fill in the ground state valence electron σ3p* —— σ3p* ——
configuration for Al2 in the one
molecular orbital diagram to the right π3p* —— —— π3p* —— ——

ENERGY
that is consistent with the fact that this π3p —— —— σ3p ——
species is paramagnetic.
σ3p —— π3p —— ——
σ3s* —— σ3s* ——
σ3s —— σ3s ——
b. The three diatomic species Al2, Al+2 , and Al−2 are predicted to have the three bond lengths 243
pm, 248 pm, and 279 pm (not necessarily in this order). Assign each of the three bond
lengths to the correct diatomic species, and briefly explain your reasoning.
Answers

1. E
2. B
3. B
4. E
5. C
6. B
7. A
8. A
9. A
10. A
11. E
0 0 -1
12. A
13. B
14. A
15. C O O
16. C S
17. B
18. A F 0
19. H H
F F O
C C
C C I
H C O O O O F F
F
N

20. H C C F

a. b.
136 pm
O O O
N N O O O
21. N N
O O 118 pm 118 pm

# equivalent resonance structures: 4 O O

 Ge
Cl Cl Cl Cl Cl
Br or
As Cl Cl
Cl Cl Cl Ge
Cl Cl
List the
22. What is the name What is the name of value(s) of the Is the molecule
Molecule of the electron the molecular ideal polar or
group geometry? geometry? (VSEPR) nonpolar?
bond angles.
AsCl3 tetrahedral Trigonal pyramidal 109.5° polar
BrCl5 octahedral Square pyramidal 90° polar
bent
GeCl2 trigonal planar 120° polar
(V-shaped, angular)

23b. Using the numbered labels (1 – 8),

indicate which atoms have the following
23a. hybridizations:

sp sp2 sp3

2 3, 4, 5
including 1 is including 6 is 7, 8
acceptable acceptable

23c. Provide the ideal bond angle predicted

by VSEPR theory for the following angles:

N1-C2-C3 C2-C3-C4 C3-C5-O6 C5-O7-C8

180° 120° 120° 109.5°

24. 867 nm

25. a. 109.5° c. 109.5° e. 109.5°

b. 120° d. 120° f. 109.5°

 a.
σ3p* ——
ENERGY
π3p* —— —— b. The higher the bond order, the shorter the bond.

σ3p —— Al2 : bond order = 1, bond length = 248 pm

26.
π3p —— —— Al+2 : bond order = 0.5, bond length = 279 pm

σ3s* —— Al−2 : bond order = 1.5, bond length = 243 pm

σ3s ——