Page 3 Continued on next page

1. When the 1s orbitals of two hydrogen atoms combine to form a hydrogen molecule, which
molecular orbitals are formed?
A. One bonding molecular orbital only
B. Two bonding molecular orbitals
C. One bonding molecular orbital and one antibonding molecular orbital correct
D. Two antibonding molecular orbitals
E. Three bonding molecular orbitals


2. The following electron configuration represents:
1s 2sp
3
2sp
3
2sp
3
2sp
3

A. the ground state of boron.
B. the sp
3
hybridized state of carbon.
C. the sp
3
hybridized state of nitrogen. correct
D. the ground state of carbon.
E. an excited state of carbon.


3. VSEPR theory predicts an identical shape for all of the following, except:
A. NH
3

B. H
3
O
+

C. BH
3
correct
D. CH
3
-

E. All have the same geometry




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4. Increasing s character makes for shorter bonds. Which is the shortest of the carbon-carbon
single bonds indicated by arrows in the following compounds?
A.
H
3
C CH
3

B.
H
3
C C CH

C.
H
3
C CH
CH
2

D.
HC C C CH
correct
E.
H
2
C
HC C CH





5. Which of the following is a set of constitutional isomers?
Br Br
Br
Br
IV III II I

A. I and II
B. II and III
C. I, II, and III
D. II, III, and IV
E. I, III, and IV correct





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6. Which of the following compounds would you expect to have the lowest boiling point?

NH
2
O

H
N
O

N
O

NH
2
O

O
N
H


A. B. C. D. E.
Ans: C

7. Which of the following ions is NOT stabilized by resonance?

O O
O
O
A
B
C
D
E


Ans: C
8. Which compound can be classified as an ester as well as a ketone?
O
O O
O
O
O
O
O
O
OH
O
I II III
IV V
OH
O



A. I B. II C. III D. IV E. V
Ans: D
Page 6 Continued on next page
9. How many 2 alkylchlorides, counting R, S stereoisomers, are possible with the formula
C
5
H
11
Cl?

A. 3
B. 4
C. 5 correct
D. 6
E. 7

10. The IR stretching frequency can be predicted to occur at the highest frequency for which of
these bonds?

A. CH correct
B. CF
C. CCl
D. CBr
E. CI

11. An organic compound which shows sharp IR absorptions at 2200 cm
-1
and 3300 cm
-1
is
likely to be what type of compound?

A. An ester
B. An alkene
C. An alkyne correct
D. An ether
E. An aldehyde


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12. Which of the acids below would have the strongest conjugate base?

A. CH
3
CH
2
OH correct
B. CH
3
CO
2
H
A. ClCH
2
CO
2
H
B. Cl
2
CHCO
2
H
C. Cl
3
CCO
2
H

13. Which acid-base reaction would not take place as written?

A. CH
3
Li + CH
3
CH
2
CH
2
CH
2
NH
2
CH
4
+ CH
3
CH
2
CH
2
CH
2
NHLi
B. CH
3
CCH + NaOCH
3
HCCNa + CH
3
OH this one
C. HCCNa + H
2
O HCCH + NaOH
D. CH
3
OH + NaNH
2
CH
3
ONa + NH
3

E. CH
3
CO
2
H + CH
3
ONa CH
3
CO
2
Na + CH
3
OH


14. The reaction of the Na salt of 3-methyl-1-pentyne with 1-bromo-3-methylbutane produces
which of these?

A. 3,8-dimethyl-4-nonyne this one
B. 2,7-dimethyl-4-nonyne
C. 3,8-dimethyl-5-nonyne
D. 3,7-dimethyl-4-nonyne
E. 3,7-dimethyl-5-nonyne


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15. Which of the following can be described as trans isomers?

CH
3
CH
2
CH
3
Cl
CH
3
Br
HO
CH
3
HO
Br
F
I II III
IV V

A. I B. II, V C. I, III, IV D. III and IV E. None of the above
Ans: C

16. The graph below shows the relative rotational energies of hexane, viewed through the C2-
C3 bond. The conformations corresponding to the 60
o
and 300
o
are:

0
o
60
o
120
o
180
o
240
o
300
o
360
o
R
e
l
a
t
i
v
e

e
n
e
r
g
y
Angle of rotation


A. Eclipsed
B. Staggered and gauche correct
C. Staggered and anti
D. More stable than the conformation at 180
o

E. None of the above




Page 9 Continued on next page
17. How many chirality centers are in Lovastatin ( Mevacor : a cholesterol-lowering drug) ?

O
HO
O
O
(Lovastatin)

A. 4
B. 5
C. 6
D. 7
E. 8 correct



18. Which compound would show optical activity?

A. cis 1,4- Dimethylcyclohexane
B. trans 1,4- Dimethylcyclohexane
C. cis 1,4- Dimethylcycloheptane
D. trans 1,4- Dimethylcycloheptane correct
E. More than one of these









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19. A solution of which of these allenes will rotate plane-polarized light?

C C C
H
H H
H
C C C
H
Cl H
H
C C C
H
Cl Cl
H
C C C
Cl
Cl Cl
H
C C C
Cl
Cl Cl
Cl
I II III
IV
V

A. I
B. II
C. III correct
D. IV
E. V
20. Which of the following molecules is/are a meso compound?

CH
3
CH
3
Br H
Br H
H
3
C
CH
3
H
H
OH
OH H
3
C
F H
H
CH
3
F
I II III

A. I
B. II
C. III
D. More than one of the above correct
E. None of the above


Page 11 Continued on next page
21. The molecules shown are:

H
CH
3
OH H
Br H
H
CH
3
OH H
H Br

A. constitutional isomers.
B. enantiomers.
C. diastereomers.
D. identical.
E. None of these
Ans: B

22. Reverse phase chromatography works on the same concepts as regular chromatography
except for one key difference: the solid phase (polar silica in regular chromatography) is
coated with a layer of NON-POLAR hydrocarbon chains. With this in mind, which of the five
compounds shown below would elute first from a REVERSE phase chromatography column,
using a 1:1 water/methanol mixture as mobile phase?

O
N
OH
A
B
C
D E





Written Questions follow
Most polar
compound (amine)
should elute first,
closely followed by
the next polar one,
cyclopentanol.