Chem 210

Practice Exam 1B

Organic Chemistry: Chem 210

Practice Exam 1B
There are 28 questions on this exam. Check that you have done all of the problems and filled in the first
28 bubbles on the scantron. Most questions are worth 4 points; there are several two-point questions
clearly labeled in the text. The maximum score on this exam is 100 points.
Instructions
Answer sheet
1) On the scantron, you need to clearly fill:
your name and your student number,
section number: (it is 001)
test form (white = test form A; yellow = test form B).
2) Use a #2 pencil
Exam policy
1) No electronic devices of any kind, such as calculators, cell phones, or even more advanced
digital watches, are allowed. Possession of such devices during the exam, whether in use
or not, is grounds for awarding a zero on the exam.
2) Molecular models are allowed (no instruction pages are permitted, however).
3) There are some blank pages at the end of the test that can be used as scratch paper.
4) Relevant tables, including the periodic table, are attached at the end of this exam.
5) Numerical values given in one question apply only to that question, and should not be used
in other questions, unless there is a specific instruction to do so. If necessary, the values
from the provided tables should be used, even if they differ from values that you may
remember from different sources.
6) The exam results are based strictly on scantrons marks. No extraneous information is used
to adjust the scores. Mark your choices with extra care.
7) Feel free to take this copy of the exam with you. The answer key will be posted on the web
after the exam (under "News").
Hints
1) As you read the question, underline or circle key words to highlight them for yourself.
2) Questions have only one correct answer, unless indicated otherwise. No partial credit will
be given.
3) There is no penalty for guessing.

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Chem 210

Practice Exam 1B

1. (4 pts) What is the name of the following hydrocarbon according to the IUPAC rules?

a)
b)
c)
d)
e)

2,6-diethyl-2-propyl-3-methylheptane
4-ethyl-4,5,8-trimethyldecane
7-ethyl-3,6,7-trimethyldecane
3,4,7-trimethyl-3-propylnonane
7-ethyl-3,4-dimethyl-3-propyloctane

2. (4 pts) Which of the following isomeric structures has the lowest energy?

a)
H

b)
CH3

CH3

H
d)
H
H 3C

c)
CH3

H
CH3

H
H

H
CH3

e)

CH3

H
H

CH3

HCH3 H CH3

3. (4 pts) The compound with the formula of C4H10O contains the alcohol functional group (OH), but has no
multiple bonds or rings. How many constitutional isomers are possible for this alcohol?
a) 2

b) 3

c) 4

d) 5

e) 6

f) 7

4. (4 pts) Which of the following is not a valid resonance structure of the others?

a)

c)

b)

d)

e)

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Chem 210

Practice Exam 1B

5. (4 pts) Which of the following molecules do not have a dipole moment?

Br

Br
Br C

H
Br
A

CH2Br2

C H

Br

Br
C C
H

Br

Br
E

a) A, D, E

b) D, E

c) A, B, C

d) D, C

e) B, D, E

6. (4 pts) The barrier to rotation about the C-C bond in bromoethane is 15 kJ/mol (3.6 kcal/mol). What energy value
can you assign to an H-Br eclipsing interaction?
a)
b)
c)
d)
e)

0.8 kcal/mol
1.0 kcal/mol
1.2 kcal/mol
1.4 kcal/mol
1.6 kcal/mol

7-10. A schematic representation of -type molecular orbitals for 3-methylene-1,4-pentadiene (built out of six
p atomic orbitals on carbon atoms) is shown below. The orbitals are arranged in random order and the
information on the relative size of orbital lobes is omitted.

3-methylene-1,4-pentadiene

a)

b)

d)

e)

7.
8.
9.
10.

c)

f)

(4 pts) Which orbital corresponds to the HOMO of 3-methylene-1,4-pentadiene?

(4 pts) Which of the orbitals has 2 nodal planes (in the bonding sense)?
(2 pts) Which of the orbitals has the highest energy?
(2 pts) Of all occupied orbitals, which one does not contribute any electron density to the third
(central) carbon?

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Chem 210

Practice Exam 1B

11. (4 pts) Which of the underlined atoms (in the molecules shown below) are of sp2-hybridization type?
A: Cl2CCCl2
a) A and D

12.

B: CH3OCH3

b) B and E

C: CH3NH2

c) A and C

D: CH3COCH3

d) C and E

E: HCCH

e) B, C, and D

(4 pts) Consider the two chair conformations of cis-1-chloro-2-methylcyclohexane. Which of the following
statements about these two isomers is true?
a) Both conformations have equally unfavorable 1,3-diaxial interactions, resulting in no net energy
difference between them.
b) The conformation with the methyl group in an equatorial position is more stable by 4.8 kJ/mol.
c) The conformation with the methyl group in an axial position is more stable by 5.2 kJ/mol.
d) The conformation with both substituents in equatorial positions is more stable by 10.4 kJ/mol.
e) The energy difference between both conformations cannot be established without knowing the value of
Cl-CH3 gauche interaction.

13-15. Consider the following reaction of boron trifluoride (BF3) and acetone:

O
BF3

product
CH3

CH3

13. (4 pts) What is the critical HOMO of this reaction?

a) nonbonding orbital on boron
b) orbital of acetone
c) orbital of acetone
d) nonbonding electron pair orbital on oxygen
14. (4 pts) What is the critical LUMO of the reaction?
a) p orbital of BF3
b) orbital of BF3
c) * orbital of acetone
d) nonbonding electron pair orbital on oxygen
15. (4 pts) Which of the following is the correct product of this reaction? (Lone electron pairs are not
shown explicitly).

a)

c)

b)
O

BF3

d)

BF3

e)
O

OH

BF3

BF3

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BF3

Chem 210

Practice Exam 1B

16-17. Consider the following species:

b) H3CCOO

a) H2CO

c) CO

d) CO32

16. (2 pts) Which one has the longest CO bond?

17. (2 pts) Which one has the shortest CO bond?

18. (4 pts) Which statement about the following equilibrium is true?

O
OH

O
+

ClO4
II

HClO4

III

IV
pKa = -10

pKa = +4

a) IV is a acting as a base
b) II is acting as an acid
c) I and III are resonance structures
d) the equilibrium favors the reactants
e) I is 14 times less acidic than IV
19. (4 pts) If stands for a wavefunction and r is the distance from the nucleus, which of the following physical
observables does the picture below represent?

(0,0)

a) electron density of a 1s orbital

b) electron density of a 2s orbital
c) electron density of a 3s orbital
d) probability of finding a proton in the nucleus
e) probability of finding an electron in the valence shell of hydrogen

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Chem 210

Practice Exam 1B

20. (4 pts) A carbon atom in H2CXY forms four bonds. It uses an sp2 hybrid to bond to X, and an sp5 hybrid to bond
to Y. The two bonds to hydrogens are made using identical hybrids. What are the hybrids that are used to
make the C-H bonds?
b) sp2

a) sp

c) sp3

d) sp4

e) sp5

21. (4 pts) Compare the hybridization of the central carbon atoms in carbon dioxide (CO2) and allene (H2CCCH2).
Which statement is correct?
a) The hybridization types of these two carbons cannot be compared because of large electronegativity
difference between carbon and oxygen in CO2 that does not exist in allene.
b) The hybridization of carbon in CO2 cannot be determined, because the lone electron pairs on oxygen do
not allow for angle measurements that are necessary to determine the hybrids involved.
c) In CO2 the carbon is sp2 hybridized, but in allene the central carbon is sp hybridized.
d) In CO2 the carbon is sp hybridized but in allene the central carbon is sp2 hybridized.
e) The central carbons in both compounds are sp hybridized.
22-23. Assume that the three structures below fully describe the carbonate ion (CO32). Note that in all of these
structures lone-pair electrons are not shown explicitly.

O
1

1
O

1
O

O
C
O
1

1 O

O 1

22. (2 pts) What is the formal charge on the top oxygen atom?
a) 1/3

b) 2/3

c) 1/2

d) 3/2

e) 1

f) 2

g) 3

f) 3

g) 4

23. (2 pts) What is the bond order of the top oxygen atom?
a) 1/3

b) 2/3

c) 4/3

d) 1

e) 2

24. (4 pts) Which of the following statements about molecular strain is correct?
a)
b)
c)
d)
e)

Cis and trans stereoisomers of substituted cycloalkanes always have equal amount of strain.
Large angle strain is present in all cycloalkanes.
Gauche strain in butane is steric in origin.
All staggered conformations of small alkanes have torsional strain.
Strained alkanes yield less heat when burned in oxygen than their strain-free isomers.

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Chem 210

Practice Exam 1B

25. (4 pts) Taking into account the standard conventions used to draw three-dimensional structures, which of the
following is the correct 3D representation of 2,3-pentadiene?
H

C C C
H3C

CH3

C C C

H3C

a)

H
CH3

H
C C C
H3C

c)

b)
H

C C C

H3C

H
CH3

d)

CH3

H
H
C C C
H3C
CH3

e)

26. (4 pts) A brilliant chemist determined the number of secondary carbons and secondary hydrogens for an
unknown alkane. Well, actually, the chemist is having trouble deciding which numbers are correct. Which
of these answers is possible for an alkane?
2o H 2o C
a)
b)
c)
d)
e)

3
4
3
3
8

3
4
5
6
4

27. (4 pts) Which of the following statements about resonance structures is false?
a)
b)
c)
d)
e)

Individual resonance structures are imaginary, not real.

Resonance forms differ only in the placement of their or nonbonding electrons.
Different resonance structures of a substance don't have to be equivalent.
The superposition of resonance forms is always more stable than any individual resonance form.
In valid resonance structures, all atoms from the second row of the periodic table must have an octet of
electrons.

28. (4 pts) Which of the following statements about valence bond (VB) and molecular orbital (MO) bonding theories
is true?
a) In VB theory only bonding orbitals are formed when bonds are made.
b) In MO theory resonance is necessary to account for delocalized electrons.
c) Electronegativity differences between bonded atoms are important in VB theory, but are totally irrelevant
in MO theory.
d) MO and VB theories almost always yield contradictory information about structure of molecules.
e) In MO theory all electrons need to be considered to understand the structure of molecules, but the
reactivity is controlled to a large degree only by the appropriate HOMOs and LUMOs in the reactants.

End of the exam

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Chem 210

Practice Exam 1B

Table 4.1 Energy Costs for Interactions in Alkane Conformers

Energy Cost
Energy Cost
Interaction
kJ/mole
kcal/mole
H-H eclipsed
4.0
1.0
H-CH3 eclipsed

6.0

1.4

CH3-CH3 eclipsed

11.0

2.6

CH3-CH3 gauche

3.8

0.9

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Chem 210

Practice Exam 1B

Page 9 of 10

Chem 210

Practice Exam 1B
Answer key: 1 B
1. C
2. D
3. C
4. D
5. B
6. E
7. A
8. A
9. D
10. B
11. A
12. B
13. D
14. A
15. A
16. D
17. C
18. D
19. B
20. C
21. E
22. B
23. C
24. C
25. B
26. E
27. E
28. E

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