Chem S-20 Practice Exam 1-A

8:10 — 9:20 a.m.

Name:

Important Notes:

1. This exam consists of 8 problems on 8 pages, plus this cover sheet, and one page for scratch work at
the end of the exam.

2. All answers must be written in the spaces provided. Do not write anything in red ink. Answers
written on the back of a page will not be graded. Anything written on the scratch page will not be graded.

3. You are allowed to use a set of molecular models for this exam.

Problem Score

1. ____________ / 12

2. ____________ / 12
Total Score:
3. ____________ / 11

4. ____________ / 16
________________ / 100
5. ____________ / 11

6. ____________ / 10

7. ____________ / 16

8. ____________ / 12
Chemistry S-20 1 Name:

1. Each of the following transformations can be carried out in one or two steps. Fill in the reagents required
for each step. If a second step is not needed, please put an "X" through the second box.

1.
a)

2.

1. OH
b)

2.

1.
c)

OH
2.

Cl

1.
d)

2.

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Chemistry S-20 2 Name:

2. Fill in the boxes with either the reactant or the product (as appropriate) of each of the indicated
transformations. Be sure to indicate the stereochemistry if it is relevant.

Br

Br2 Br
a)

OH
b)
H+

Br2
c)
CH3OH

1. O3
d)

2. (CH3)2S

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Chemistry S-20 3 Name:

3. Circle and identify all the functional groups in the compound below. Then write the hybridization of each
of the indicated atoms in the boxes provided. (This compound is the pharmaceutical enalapril, which is used
to lower blood pressure.)

O
O O OH
H
N
O N

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Chemistry S-20 4 Name:

4. Consider the following acid-base equilibrium:

O OH OH O
+ +
Keq = 105
phenol cyclohexanol
a) Based on the information above and on what you know about pKa values, estimate the pKa of phenol.

pKa of phenol:

b) Circle the appropriate phrase to complete the following sentence:

more just as less

Compared with cyclohexanol, the compound phenol is:
acidic acidic acidic

c) Explain your answer to part (b) above. Provide both a resonance explanation and an explanation that
considers the molecular orbitals of these species. (Hint: consider the structure and stability of the conjugate
base for each of these species.) Clear structures and diagrams will be essential!

Resonance Explanation: Frontier Molecular Orbital Explanation:

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Chemistry S-20 5 Name:

5. Consider the following chemical transformation. For each step in this mechanism, provide the curved arrows
necessary to get from the reactants to the products. Be sure to indicate lone pairs or hydrogen atoms on any
species if necessary. (Hint: Focus on each step individually; we will grade each step independently.)

Just to be clear, the overall reaction is:

Br 1. PBr3
+ P OH
2. NaOEt
OH Br Br

Br

P + Br–
O Br
H

+ HOPBr2
Br

+ HO + Br–

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Chemistry S-20 6 Name:

6. The following "name" does, indeed, describe an alkene. However, the name is not the correct systematic
name for the compound.

(Z)-2,3-di-tert-butyl-3-hexene

a) Provide the skeletal structure that could be described by this name.

b) Provide the best possible systematic name for the alkene described by the incorrect name given above.

c) For the compound illustrated below, draw a Newman projection to show the lowest-energy conformation
around the single bond indicated in bold. If there is more than one conformation of lowest energy, please draw
all such conformations.

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Chemistry S-20
7 Name:

7. The following rather interesting reaction has been observed:

O
Br2
Br + HBr
HO

Draw a complete curved-arrow mechanism for this reaction. For every step, identify all the frontier molecular
orbital (donor/acceptor) interactions involved. (You only need to name the orbitals, e.g., !*CO. Neither "cartoon"
orbital drawings nor energy-level diagrams are necessary.) You do not need to worry about stereochemistry.
Be sure that your mechanism can account for both products observed in this reaction.

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Chemistry S-20
8 Name:

8. Provide a complete synthesis of the following desired product starting from any hydrocarbons you
choose. You may also use any inorganic reagents. You do not need to show any mechanisms. The correct
answer will require 4 or fewer total steps.

Starting Material: any hydrocarbons you choose.

Desired Product

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SCRATCH PAPER ONLY - NOTHING ON THIS SHEET WILL BE GRADED