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Organic Chemistry 1 (CHE 230):

Exam 3 Autumn Quarter 2015
Drs. Kyle A. Grice & Paul A. Vadola

name:___________________________________

Instructions: no exceptions will be made to the following guidelines

a. Please answer each of the following questions as neatly and completely as possible in the spaces provided.
b. Place structures in the boxes and answers on the lines provided when asked.
c. No exams completed in pencil are eligible for a re-grade.
d. If a re-grade of a specific question is requested the entire exam will be re-graded.
1. Consider the following molecules when answering questions a-c below:

a. When compound A reacts with NaOMe in THF the product is a single chiral substitution compound B.
When A reacts with MeOH B also forms, but the rate of reaction is substantially slower. Determine which
compound above is A and write A in the box provided. [2 pts]
b. When compound C reacts with NaOMe in THF the product is a single chiral substitution compound D.
When C reacts with MeOH the result is a mixture of stereoisomers B and D. Determine which compound
above is C and write C in the box provided. [2 pts]
c. Draw products B and D in the boxes below. [3 pts]

product B

product D

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2. The ether below can be synthesized from the alkyl bromide shown by nucleophilic substitution, either SN1
or SN2. However, these mechanisms require rather different reaction parameters.
a. Fill-in the table below with the information needed for the reaction to proceed by an SN1 and an SN2
mechanism. [12 pts]

b. Draw the SN1 mechanism for the conversion of 3-iodo-pentane to 3-methoxy-pentane. (note: Be sure to
include any and all intermediates and curved arrows. Assume all products are neutral molecules). [6 pts]

c. Draw the transition state for the SN2 reaction. [2 pts]

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3. The two isomeric alkyl bromides A and B shown below undergo E2 elimination reactions at dramatically
different rates:

a. Circle the isomer that undergoes elimination faster. [2 pts]

b. Provide the name of compound A on the line below. [2 pts]
IUPAC name of A here:________________________________________________________________
c. Draw the slower isomer in its reactive chair conformation and in no more than TWO sentences explain
why this isomer undergoes E2 slowly. [2 + 2 pts]
Explanation here:

chair structure here

4. When isobutyl bromide is dissolved in (CH3CH2)3N and heated, a salt precipitates. Draw a mechanism for
this reaction using curved arrows to indicate electron flow and draw the product. [3 pts]

5. a. Predict the product of the reaction below and draw it in the box provided. [3 pts]

b. Draw the mechanism for this reaction. [3 pts]

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6. Circle the conformer(s) below that can react via an E2 mechanism. [2 pts]

7. Circle the alkyl halide(s) below that yield a racemate upon reaction with dimethylamine (Me2NH). [2 pts]

8. Carbocations are key intermediates in many reactions, including some you have learned already. Circle the
carbocation below that will form the fastest. [2 pts]

9. Complete the reaction sequences below by providing the missing starting materials, reagents, solvents,
and products. If more than one product forms draw all of them. If no reaction occurs write no reaction or
N.R. in the box. [26 pts]
A

MAJOR product
reaction a
B

ONLY product
reaction b

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D
KOtBu (2 equivalents)
THF

THF

10. How many CO and CN bonds in Prozac can be formed by SN2 reactions: [3 pts]:
a. 0
b. 1
c. 2
d. 3
e. 4
11. How many CO and CN bonds in Prozac can be formed by SN1 reactions: [3 pts]:
a. 0
b. 1
c. 2
d. 3
e. 4
12. Which of the following compounds can act as bases in E2 reactions: [3 pts]:
a. NaOMe
b. KNH2
c. LDA
d. NaCN
e. KI

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13. Which of the following compounds can act as nucleophiles in SN2 reactions: [3 pts]:
a. NaOMe
b. KNH2
c. LDA
d. NaCN
e. KI
14. Which of the following ions would be most nucleophilic in methanol: [3 pts]:
a. Clb. Ic. Brd. F15. Reactions using methyl iodide as the alkyl halide are often performed in neat methyl iodide (with methyl
iodide as the solvent). What type of solvent is it? [3 pts]:
a. nonpolar aprotic
b. polar protic
c. polar aprotic
d. Thats no solvent . . . its a space station
e. nonpolar protic
16. How many different E2 products are possible from the following alkyl iodide: [3 pts]
a. 0
b. 1
c. 2
d. 3
e. 4
17. How many different elimination products are possible from the following alkyl bromide: [3 pts]
a. 0
b. 1
c. 2
d. 3
e. 4

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BONUS: The Arbuzov reaction converts trialkyl phsophites to dialkyl phosphonates, which are highly
useful synthetic intermediates for the synthesis of alkenes. While the overall transformation may appear
complex you have already learned all of the chemistry needed to propose a mechanism for this reaction, so
give it a shot! Propose a reasonable reaction mechanism using curved arrow notation to illustrate the flow of
electrons [5 pts].