1. (3pt) Draw a s orbital, a p orbital, an a single sp3 orbital in the spaces provided
(assume the nucleus is at the center of the axis)
2. (4pt) Fill the valence electron shells for the following atoms:
2p
Nitrogen, N
2s
2p
Carbon, C
2s
3. (3pt) Write the ground state electron configurations for the following.
Boron, B
Sodium, Na
Oxide ion, O2-
4. (3pt) Draw Lewis structures for the following molecules using dots to indicate both
covalent bonds and lone pairs.
AlCl3
H3CCN
N3-
5. (3pt) Ethylene (CH2CH2) has a single C-C double bond. Draw the p orbitals on
ethylene and indicate how they interact to form a  bond (only  bonds are shown below)
H
H
C
C
H
H
6. (3pt) Explain why cyclopropane is a relatively unstable molecule.
H
H
C
H
C
H
H
C
H
7. (6pt) Give the hybridization for the circled non-hydrogen atoms
Norethynodrel
The first oral contraceptive
3
Vitamin B6
CH
6
4
OH
H
O
C
H
CH2
H
O
C
H
HO
HO
O
2
N
5
1
1______________________
2______________________
3______________________
4______________________
5______________________
6______________________
8. (3pt) Arrange the following molecules in increasing bond strength.
HC
N
H3C
NH2
H2 C
Circle the molecule that has the shortest C-N bond.
NH
OH
P
O
9. (3pt) Give the bond angles for each of the indicated carbons:
Norethynodrel
3
OH
2
H
O
H
C
1. ________________________
CH
2. ________________________
C
3. ________________________
H
1
10. (6pt) Indicate the direction of each molecule’s overall dipole moment. Leave
molecules without a dipole moment blank.
H
Br
C
H
C
H
O
Cl
Cl
Al
Cl
S
C
OH
Li
O
H3C
H3C
H3C
CH3
CH3
CH3
CH3
11. (4pt) Dichloromethane (CH2Cl2) has a dipole moment, but carbon tetrachloride
(CCl4) does not, explain why.
12. (4pt) Calculate the formal charges for the following (lone pairs are shown, charges
are not):
O
* O
N
F
O
H
N_____________
*O____________
F
B
O
F
B____________
O_____________
13. (7pt) Show all resonance forms for the following using correct arrows indicate
electron movement and differentiate between resonance forms:
O
O
O
O
H
H
H
14.(3pt) Draw an arrow (doesn’t matter what kind) in the direction you would expect
each equilibrium to proceed (pKa’s are given for each acidic species).
+
+
N
H
N
15
44
O
H3
O+
O
+
+
H2O
-1.7
O
OH
4.76
O
+
+
OH
O
O
N
HN
17
14.7
O
O
15. (2pt) Circle which has the strongest conjugate base.
NO2
or
NH2
O
or
O2N
NO2
pKa 8.3
pKa 21
NH3
pKa 41
pKa -9.3
16. (6pt) Use correct arrows to show the electron flow and predict the products of these
two reactions
+
OH
N
H
H
H
N
Cl
Cl
Al
+
H
Cl
17. (4pt) Indicate which molecules are isomers by circling the pair. Leave non-isomers
pairs blank.
O
and
OH
and
O
O
and
H
O
HO
O
HO
O
and
O
18. (5pt) List all intermolecular forces you would expect in the following compounds,
circle the compounds you would expect to be hydrophilic.
O
OH
Cl
C
Cl
Cl
Cl
O
19. (6pt) Name the indicated functional groups
Prozac
1
Vitamin B6
3
H
N
6
5
O
H
O
HO
4
F
HO
O
2
F
F
N
1______________________
2_____________________
3______________________
4______________________
5______________________
6______________________
OH
P
O
20. (6pt) Draw the following molecules:
sec-butyl chloride (an alkyl halide)
iso-pentyl alcohol
tert-butyl thiol
21. (9pt) Name the following molecules:
22. (7pt) Consider 1-bromoethane (BrCH2CH2CH3)
Draw a Newman projection through the C2-C3 bond in the following conformations:
Anti
Gauche
Two different eclipsed
Given the following information, calculate the barrier to rotation of the most strained
eclipsed conformer.
Interaction
H-H eclipsed
C-H eclipsed
C-C eclipsed
Br-C eclipsed
Energy
4.0 kJ/mol
6.0 kJ/mol
11.0 kJ/mol
13.0 kJ/mol
Bonus (4pt) Give a molecule of the day’s chemical name and describe its use.
Bonus (2pt) Below is a molecule used on a promotional bag for the 2007 ACS Regional
Meeting. Circle and identify the mistake in this molecule:
OH
O
S