Chem 231

Final Exam
Dr. O.
NAME __________________________________________________

Spring 2009
page 1

1. Shown below are 13 different bonding scenarios for boron, carbon, nitrogen, oxygen and
halogen. Write all non-zero formal charges next to the appropriate atoms.

(X = F, Cl, Br, I)

2. For each of the following:

i. indicate the total number of valence electrons for the formula given
ii. draw a Lewis structure to show all covalent bonds
iii. show all lone pair electrons
iv. write non-zero formal charges on appropriate atoms
a. HSO4-1 (v.e. ___)

b. NH3BF3 (v.e. ___)

c. HNO3 (v.e. ___)

d. CH2 (carbene) (v.e. ___)

Chem231
Final Exam
First Name ______________________________________________________________

Spring 2009
Page 2

3. a. Push arrows to show how at least 4 resonance structures can be drawn for this structure:
H3C

OCH3

H3C

b. Which of your structures is the greatest contributor to the resonance hybrid?

4. Match each of the 4 orbital diagrams with an element from the 2 nd period.

2p
2s
1s

5. Shown below is the structure of a pentyl group indicating the missing valence.
CH3

CH2

CH2

CH2

CH2

n-pentyl group

Provide names for the following groups:

CH3

CH3
a. CH3 CH2

d. CH3 CH

CH2

CH3

CH2

b. CH CH CH
3
2

e. CH3

CH2

CH

CH3

c. CH3 C

f. CH3

CH3

CH2 CH2

Chem231
Final Exam
First Name ______________________________________________________________

Spring 2009
Page 3

6. Examine the following Newman projections:

H
H

CH3

CH3
A

H
H

CH3
H

H CH3

CH3

H
H
B

CH3

H3C CH3
H
H

a. Which structure (A,B,C or D) is eclipsed?

i. A and B
ii. A, B and D
iii. B and C
iv. C and D
v. only D
b. Which structure (A,B,C or D) is anti?
i. A and B
ii. A and C
iii. only A
iv. only D
v. all of them
c. Which structure has the highest potential
energy?
i. A and B
ii. A and C
iii. only A
iv. only D
v. C and D

H
H
D

d. Which structure (A,B,C or D) is staggered?

i. A and B
ii. A, B and D
iii. B and C
iv. C and D
v. all of them
e. Which structure (A,B,C or D) is syn?
i. only D
ii. A and C
iii. only A
iv. B and C
v. all of them
f. Which structure has the lowest potential
energy?
i. A and B
ii. A and C
iii. only A
iv. only D
v. C and D

7. Draw a Newman projection for cis-1,2-dimethylcyclohexane.

8. Draw the chair conformation for trans-1,3-dichlorocyclohexane and include all axial and
equatorial hydrogen atoms. You must show correct bond angles- no partial credit.

Chem231
Final Exam
First Name ______________________________________________________________

Spring 2009
Page 4

9. Circle the molecules that are chiral:

H

CH3
CH3

H3C

H
O

CH
CH3

OH

OH

OH

H
OH

10. Assign absolute stereochemistry (R or S) to the following:

Cl

CH2CH3

CH3

H
CH3

CH2CH3

CH3
CH
CH3

CH3

CH3

Br
Cl

CH(CH3)2

O
C

HO

H
CH2OH

11. What is the maximum number of stereoisomers possible for a molecule that has four
asymmetric centers? ____
12. Consider 2,3 dibromobutane CH3 -CHBr-CHBr-CH3
a. Draw a Fischer projection for all possible stereoisomers
b. Assign absolute stereochemistry to each chiral center on each structure
c. Identify one pair enantiomers
d. Identify one pair of diastereomers
e. Identify all meso structures
f. How many stereoisomers actually exist for this molecule? ____

Chem231
Final Exam
First Name ______________________________________________________________

Spring 2009
Page 5

13. Draw both addition products and indicate which is the Markovnikov product.
CH3
C

HCl

CH2

CH3

14. Elimination of HBr from 2-bromo-2-methylbutane gives a 70/30 ratio of isomeric alkenes:

70%

Br

CH3CH2O

CH3

CH2

CH3

CH3

30%

a. Circle all -hydrogen atoms in the substrate.

b. Draw both products and indicate which is the Zaitzev product.
c. How can this ratio be reversed?

15. Draw the complete mechanism (arrow pushing) to show how this rearrangement occurs:
CH3 H
CH3

C
OH

CH3
CH2CH3

H3O

CH3

CH2CH3

Chem231
Final Exam
First Name ______________________________________________________________

Spring 2009
Page 6

16. Reactions of alkenes and alkynes- Write the structure of the major organic product for each
reaction. Indicate stereochemistry and regiochemistry where indicated.
Br

CH3

Br

H2/Pd
CH3OH

CH3

a.

CH3

HCl

b.

indicate stereochemistry

indicate regiochemistry

CH3

c.

HBr
peroxides

indicate regiochemistry

CH3
CH3

H+
H2O

d.

indicate regiochemistry

1) Hg(OAc)2/H2O
2) NaBH4

CH3

e.

indicate regiochemistry

H
C
C

f.

CH3

1) BH3/THF
CH3 2) H2O2, OH

CH3

g.

h. CH

indicate regiochemistry

CH2
indicate stereochemistry

CH3

HCl

indicate regiochemistry

Chem231
Final Exam
First Name ______________________________________________________________

CH3

1) O3
2) Zn or DMS

i.

OsO4

j.

CH3

indicate stereochemistry

KMnO4

k.

CH3

conc., hot

KMnO4
cold, dilute

l.

H2O, OH-

CH3

indicate stereochemistry

O
O

CH3

CH3

CH3CO2H

m.

indicate stereochemistry

Br2

n.

CH2Cl2

indicate stereochemistry

Br2

o.

CH3

H2O

indicate stereochemistry
and regiochemistry

Spring 2009
Page 7

Chem231
Final Exam
First Name ______________________________________________________________

Spring 2009
Page 8

17. Addition Reactions and reduction reactions of carbonyl compounds. Draw the product or
write NR if no reaction is expected.
O
C

Li

2) H3O+

a.

b.

H3C

2) H3O+

1)

CH3

1)

LiAlH4
THF

2) H3O+

c.

O
C

OCH3

2) H3O+

d.

CH3

e.

NaBH4
CH3OH

1)

OCH3

CH3

CH

CH2

1)

NaBH4
CH3OH

2) H3O+

f.

18. Complete these reactions:

NaNH2
OH

NH3 (liq)

OH
CH2

H2SO4

1)
CH3

Mg/THF
CH3Br

2) H3O+

Chem231
Final Exam
First Name ______________________________________________________________

Spring 2009
Page 9

19. Match the following molecules with each of the 1H NMR spectra; there is one spectrum for
each molecule. Draw the molecule on the spectrum. Integration is shown above each signal.
O

OH
CH3

CH3

CH2

CH

CH2

CH2

CH3

CH3
O

O
CH3

CH2

CH3

CH3

CH3

O
CH2

OH

Chem231
Final Exam
First Name ______________________________________________________________

Spring 2009
Page 10