CHEMISTRY 241

EXAMINATION II
Wednesday, March 2, 2011 Professor William P. Dailey

NAME:_____________________________________________________________
Student ID number :___________________________________________________
Recitation Section (circle one): Monday Tuesday Wednesday

QUESTIONS POINTS SCORE

1. 12 ______
2. 13 ______
3. 15 ______

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4. 15 ______

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5. 15 ______

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6. 14 ______
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7. 16 ______
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TOTAL ______
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READ ALL QUESTIONS CAREFULLY BEFORE ANSWERING THEM.

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 1. (12 points) Draw structural representations of each of the following molecules. Be sure that your
drawing shows the configuration at each stereocenter.

a. (R)-3-methylhexane

b. (1R, 2R)-1-Ethyl-2-fluorocyclopropane

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2. (13 Points) An apparent exception to the Saytzeff rule can be found in the elimination reaction of
2-bromo-2,4,4-trimethylpentane, which reacts with potassium ethoxide to yield an alkene mixture
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containing 86 percent 2,4,4-trimethyl-1-pentene and 14 percent 2,4,4,trimethyl-2-pentene. Draw out the

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reaction and the products (No mechanism needed). The heats of hydrogenation of the two alkenes are
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-27.2 and -28.4 kcal/mol, respectively. Suggest an explanation for the observation that the major alkene
is the one with the less highly substituted double bond and clearly explain why this should NOT be
considered an exception to the Saytzeff rule. (Hint: What is the basis of the Saytzeff rule?)
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 3. (15 Points) Write the products of E2 elimination for each of the following isomeric halogenated
compounds.

Ph
H Br
A.

C H3 H
Ph

Ph

B.
H Br

H C H3
Ph

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One of these compounds undergoes elimination at a rate fifty times as fast as the other. Which

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one is it? Why?

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4. (15 points) Write a complete arrow pushing mechanism for the following reaction.
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 5. (15 points total) When 1-fluorocyclohexene (1) is treated with N-bromosuccinimide (NBS) under
free radical conditions, the products 2, 3, and 4 result. Using an appropriate arrow pushing mechanism,
explain this observation. For simplicity, assume that a low concentration of Br2 is used as the
reagent rather than NBS.

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 6. (14 points total) a. Explain why chloromethyl methyl ether (ClCH2OCH3) undergoes rapid SN1
reaction while 1-chloropropane is totally unreactive under similar conditions.

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b. Compound A reacts faster than compound B under SN2 conditions. Explain this difference.
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 7. (16 points) Draw the structure of the alkyl bromide (an alkane or cycloalkane containing only
carbon, hydrogen and bromine) and give the reagent(s) that would produce ONLY the following
products. You don't need to show any mechanisms.

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