CHEMISTRY 242

EXAMINATION I
Friday, February 10, 2017 Professor William P. Dailey

NAME:_____________________________________________________________
My signature below certifies that I have complied with the University of Pennsylvania's Code of
Academic Integrity in completing this examination.

___________________________________ ______________
Signature Date

Student ID number:____________________________________________________
Recitation Section (circle one): Monday Wed Friday(rm109) Friday(rm514)
QUESTIONS POINTS SCORE

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1. 8 ______

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2. 10 ______

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3. 14 ______

o.
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4. 10 ______
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5. 8 ______
6. 14 ______
o
aC s

7. 36 ______
vi y re

TOTAL ______
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READ ALL QUESTIONS CAREFULLY BEFORE ANSWERING THEM.

Make sure to show stereochemistry, if appropriate.
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 1. (8 points) Label each of the following molecules as aromatic, anti-aromatic or non-aromatic.

B S
N
N

2. (10 points) Azulene is an unusual polycyclic unsaturated hydrocarbon with a resonance energy
of about 50 kcal/mol (207 kJ/mol). Unlike most unsaturated hydrocarbons, azulene exhibits a large
molecular dipole moment of 1.0 D. Explain why azulene has such a large dipole moment, and draw the
direction of the molecular dipole moment based on your explanation.

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 3. (14 points) a. The following reaction sequence does not work as written. Predict the actual product
that is obtained and very briefly explain why it will be formed instead of the product written.
1. CH 3Li
H HO
HO
2. CH 3CH2Br

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b. Propose a viable alternative synthetic sequence that will allow you to get from the starting
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material to the written product. You may use any organic or inorganic reagents and you don't need to
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show any mechanisms.
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 4. (10 points) Provide a complete molecular orbital energy level diagram for the pi molecular orbitals of
the cyclopropenyl cation. Draw out all the molecular orbitals and place the appropriate number of pi
electrons into the appropriate orbital(s). Label the Highest Occupied Molecular Orbital and the Lowest
Unoccupied Molecular Orbital.

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 5. (8 points) Provide a complete mechanism using the curved-arrow formalism to explain the following
reaction.

200 oC

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 6. (14 points) Propose a viable synthesis of the following racemic molecule using starting materials
containing only 4 carbons atoms or less. (All organic starting materials and/or reagents can only have
4 or fewer carbon atoms.) You may use any inorganic reagents, and you don't need to show any
mechanisms.

OH

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 7. (36 points total) Provide structures for the products of the following reactions. If more than one
product is expected, then note the major and minor products. If no reaction is expected, then say so.
You don't need to show any mechanisms.

NaOH (1 equiv)
Br SH

O
N Br
O
heat,light

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O O
+
OCH3 heat
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CF 3
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Cl2

AlCl3
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NO 2
H2

Pd/C

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 Question 7 continued.

mCPBA

m
O CH 3ONa (0.01 equiv.)

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CH 3OH

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hν
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O HBr (excess)

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