Exam 2 – CHEM231 51XX 50 minutes Stocker – Spring 2022

Name: _______________________________

Circle your discussion: Monday/Wednesday

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 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

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Exam 2 – CHEM231 51XX 50 minutes Stocker – Spring 2022

Page 3: _____/24 Page 6: _____/17

Page 4: _____/16 Page 7: _____/15

Page 5: _____/13 Page 8: _____/15

TOTAL POINTS: _____/100

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Exam 2 – CHEM231 51XX 50 minutes Stocker – Spring 2022

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

N
O H
H
Cl
OH OH

_______ _______ _______

2. Circle the nucleophile that will react the fastest in an SN2 mechanism with a
primary alkyl halide in a polar aprotic solvent. (4 pt)

H2 O HF HI CH3OH LiSH KOH

3. Circle all bases that will go through an E1 mechanism when heated in the
presence of a secondary alkyl halide. (4 pt)

H2 O LiN3 KOH CH3OH NaSH KNH2

4. For the reactions shown below, circle all reactants that could undergo an SN2
mechanism with KN3. (6 pt)

I
Br
Cl

OCH3
OH
Cl

5. Draw the structure of the most stable intermediate for the reaction shown below.
(7 pt)

NaBr

Cl

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Exam 2 – CHEM231 51XX 50 minutes Stocker – Spring 2022

6. Answer the following questions for the reaction shown below.

HBr

a. Is the reaction above exothermic or endothermic? Briefly explain your reasoning

either qualitatively or quantitatively. (5 pt)

b. Draw the structure of the transition state for the rate-determining step for the
reaction shown above. (6 pt)

c. Circle the reaction coordinate for the reaction shown above. (5 pt)

ΔH

ΔH ΔH

Progress of reaction Progress of reaction Progress of reaction

ΔH
ΔH ΔH

Progress of reaction
Progress of reaction Progress of reaction

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Exam 2 – CHEM231 51XX 50 minutes Stocker – Spring 2022

7. Explain why the intermediate was formed in the mechanistic step shown below.
(7 pt)

8. Circle all major product(s) for the reaction shown below. Hint: Use a diagram to
determine the major product(s). (6 pt)

Cl NaOH

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Exam 2 – CHEM231 51XX 50 minutes Stocker – Spring 2022

9. Draw a detailed mechanism, using arrow formalisms, for the reaction shown
below. Be sure to include all resonance structures, where appropriate. Hint: The
reaction goes through an intramolecular reaction. (10 pt)

Cl
Reflux
OH O

10. Propose a series of reactions to accomplish the following synthesis. Be sure to

include the starting material(s), reagent(s), and product(s) for each step. Do not
write the mechanism or mechanistic intermediates for each reaction. (7 pt)

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Exam 2 – CHEM231 51XX 50 minutes Stocker – Spring 2022

11. 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.) (30 pt)

a.

Br
CH3OH
Cl

b.

OH

c.

I 1) KOCH2CH3

Cl 2) Br2, CCl4

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Exam 2 – CHEM231 51XX 50 minutes Stocker – Spring 2022

d.

H3O+

e.

I
1) H2, Pd
2) NaCN

f.

1) Cl2, Δ

2) KOC(CH3)3

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Exam 2 – CHEM231 51XX 50 minutes Stocker – Spring 2022

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