Exam 2 – CHEM231 53XX 50 minutes Stocker – Spring 2019

Name: _______________________________

Please copy and sign the honor pledge below:

“I pledge on my honor that I have not given or received any unauthorized assistance on this examination”

Signature Date

Directions:
Show all of your work when solving problems. Be sure to clearly report your final answer that will be
graded. You may do this by circling your answer. Cross out any work that you do not want graded.
No credit will be given where multiple answers are shown. If your explanation for a question is
resonance, you must draw out the resonance structures to receive full credit. Provide diagrams,
drawings, or structures for short answer questions when applicable. Only exams written entirely in pen
will be considered for a regrade. A table of approximate bond dissociate energies is shown below.

Bond Bond Energy (kJ/mol) Bond Bond Energy (kJ/mol)

C–H 400 C–O 350
O–H 450 C – Cl 350
C–C 350 C – Br 300
C=C 600 Br – Br 200
C–N 300 H – Br 350

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Exam 2 – CHEM231 53XX 50 minutes Stocker – Spring 2019

Page 3: _____/14 Page 6: _____/10

Page 4: _____/25 Page 7: _____/20

Page 5: _____/8 Page 8: _____/23

TOTAL POINTS: _____/100

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Exam 2 – CHEM231 53XX 50 minutes Stocker – Spring 2019

1. Provide the pKa’s for the underlined protons. (3 pt)

O
H HO
N
Br
OH2

_______ _______ _______

2. Answer the following questions using the reaction shown below.

OH OH

ONa OH
+ +

a. Determine the equilibrium constant for the reaction shown above. (2 pt)
Keq = ________

b. Circle the equilibrium arrow that corresponds to your equilibrium

constant determined in part a. (2 pt)

3. Determine which mechanism the following reactions undergo. (4 pt)

a.
Cl

KOH
SN1 SN2 E1 E2
H 2O

b.

KCN SN1 SN2 E1 E2

Δ
Br

4. Determine the equilibrium arrow for the ring flip of the chair conformer below. (3 pt)

OCH3 Br

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Exam 2 – CHEM231 53XX 50 minutes Stocker – Spring 2019

5. Draw the exact ring flip of the following chair conformer. (7 pt)
HO
O

OH

OCH3

6. Fully explain why the following reaction is regioselective. (8 pt)

HBr

7. Draw the reaction coordinate for the reaction shown below. Clearly draw your diagram
and label transition state(s) as and structure(s) of all intermediate(s) where
appropriate. (10 pt)

OH
Δ
Br

ΔH

Progress of Reaction

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Exam 2 – CHEM231 53XX 50 minutes Stocker – Spring 2019

8. Match the IR spectrum for both the starting material and the product for the following
reaction. Place your answer in the boxes provided. (8 pt)

OCH3

H3O+
Product(s)
IR Spectrum IR Spectrum

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Exam 2 – CHEM231 53XX 50 minutes Stocker – Spring 2019

9. Draw a detailed mechanism, using arrow formalisms, for the reaction shown below. Be
sure to include all resonance structures, where appropriate. (10 pt)
Cl Cl

Br Br
HCl
Cl Cl
Br

Br Br

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Exam 2 – CHEM231 53XX 50 minutes Stocker – Spring 2019

10. Provide the appropriate starting material(s), reagent(s), or product(s) as required. If

more than one product can be formed, draw only the major product. Indicate
stereochemistry where appropriate. Some reactions may require more than one step.
(Assume excess reagent is present, unless otherwise noted.) (43 pt)
a.

CN
1) HBr
2) NaOC(CH3)3

b.

HO
1) Cl2, H2O
2) KN3, Δ

c.

Br
1 equivalent Cl2
CCl4

d.

Br
H 2O

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Exam 2 – CHEM231 53XX 50 minutes Stocker – Spring 2019

e.

OH
Br Br

f.

OH

H2
Pd

g.

CH3OH
H+

h.

Cl 1 equivalent Br2
Δ

i.
CH3OH
Δ

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