Exam 2 – CHEM231 52XX 50 minutes Stocker – Fall 2021

Name: _______________________________

Please 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. Tables of approximate bond dissociate energies and A-values are
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

Group A-Values (kcal/mol) Group A-Values (kcal/mol)

–Cl 0.48 –COOH 1.35
–Cl 0.43 –CH3 1.7
–OH 0.87 –CH2CH3 1.75
–OCH3 0.67 –CN 0.21
–OCH2CH3 0.9 –C(CH3)3 4.9

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Exam 2 – CHEM231 52XX 50 minutes Stocker – Fall 2021

Page 3: _____/18 Page 6: _____/16

Page 4: _____/18 Page 7: _____/14

Page 5: _____/15 Page 8: _____/19

TOTAL POINTS: _____/100

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Exam 2 – CHEM231 52XX 50 minutes Stocker – Fall 2021

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

O
NH2
O
H3CO

OH
O
Cl H

_______ _______ _______

2. Circle the equilibrium constant that matches the chair conformer and its ring flip. (3 pt)
OCH3

O
HO

Cl
HO O

Keq = 10-3 Keq = 103 Keq = 100

3. Determine whether the following reactions are stereoselective. (6 pt)

a. (R)-2-bromohexane reacts with KCl in acetone. YES/NO

b. 3,4-dimethylcyclohex-1-ene reacts with 1) Hg(OAc)2, H2O. YES/NO

c. 3,4-dimethylcyclohex-1-ene reacts with 1) BH3, THF 2) H2O2, NaOH. YES/NO

4. Determine which mechanism the following reactions undergo AND include an

appropriate solvent for that mechanism. (i.e. choose a solvent that increases the rate
of the reaction) (6 pt)
a.
Br

KCN
SN1 SN2 E1 E2

b.

OCH3 OH
SN1 SN2 E1 E2
Δ
Cl

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Exam 2 – CHEM231 52XX 50 minutes Stocker – Fall 2021

5. Answer the following questions for the reaction coordinate shown below.

ΔH

Progress of reaction
a. Label the transition state(s) ( ) on the reaction coordinate shown above. (2 pt)

b. Label the intermediate(s) (I) on the reaction coordinate shown above. (2 pt)

c. Label the rate-determining step on the reaction coordinate shown above. (2 pt)

d. Determine whether the following steps are endothermic or exothermic using the
reaction coordinate shown above. (2 pt)

Step 1: exo/endo Step 2: exo/endo

6. Draw the exact ring flip for the following chair conformer. (5 pt)

OCH3
N

Cl

7. Draw the transition state for the following step. (5 pt)

OH
O H

OH2
H 2O

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Exam 2 – CHEM231 52XX 50 minutes Stocker – Fall 2021

8. Which intermediate is more stable? Circle your choice and fully explain. (7 pt)

A B C D

9. Draw the reaction coordinate for the reaction shown below. Include the
structure(s) of all intermediate(s) in your diagram where appropriate. (8 pt)
Cl H 2O OH
Δ

OH2

ΔH

Progress of Reaction

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Exam 2 – CHEM231 52XX 50 minutes Stocker – Fall 2021

10. Draw the structure of the most stable intermediate that would form from the
following carbocation. (6 pt)

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

EtOH
H+

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Exam 2 – CHEM231 52XX 50 minutes Stocker – Fall 2021

12. 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.) (33 pt)

a.

Br

1) LiOC(CH3)3

I 2) Cl2, CH2Cl2

b.
Cl Cl

HO

c.

Br

1) D2, Rh

2) NaCN
H3CO 3) HBr, H2O2, Δ

Cl

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Exam 2 – CHEM231 52XX 50 minutes Stocker – Fall 2021

d.

OCH3

1) Br2, Δ

2) NaOCH3, DMSO
Cl

e.

Cl

HI

f.

1) BD3, THF

I 2) KOH, H2O2
OCH3

g.

Br

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Exam 2 – CHEM231 52XX 50 minutes Stocker – Fall 2021

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