CHE 321 Organic Chemistry 1
Exam 2 Form 1
Thursday October 27, 2016
8:45 PM – 10:15 PM
1. Write your nine digit University ID number in the space provided and then bubble in
each of the nine digits.
2. Print your name and sign your answer form using the spaces provided.
3. Questions 1 to 10 are 5 point multiple choice questions. Bubble your answers on the
answer form. Questions 11-17 are short answer questions with points as indicated. Write
out your answers in the indicated place on the answer form.
Exam 2 Form 1 CHE 321 Fall 2016
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1. Which of the following isomeric alkenes is the most stable?
C
2. Predict the product of the following reaction.
D
3. Select the order that has the following carbocations correctly arranged with respect to
increasing stability.
A
Exam 2 Form 1 CHE 321 Fall 2016
4. Select the correct IUPAC name of the following compound.
A.
B.
C.
D.
E.
F.
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F
(3R,7R,E)-5-Ethyl-3,7-dimethyl-4-nonene
(3S,7S,E)-5-Ethyl-3,7-dimethyl-4-nonene
(3R,7S,E)-5-Ethyl-3,7-dimethyl-4-nonene
(3S,7S,Z)-5-Ethyl-3,7-dimethyl-4-nonene
(3R,7S,Z)-5-Ethyl-3,7-dimethyl-4-nonene
(3S,7R,Z)-5-Ethyl-3,7-dimethyl-4-nonene
5. Choose the major product of the following reaction.
E
6. Select the order that has the following compounds correctly arranged with respect to increasing
solubility in water.
B
Exam 2 Form 1 CHE 321 Fall 2016
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7. The following is an example of a radical reaction where a functional group is removed and
replaced by a hydrogen atom. The initiation step is shown below.
E
Choose the radical intermediates that take part in the propagation steps of the reaction.
A. 1 and 3
B. 1 and 4
C. 1 and 5
D. 2 and 3
E. 2 and 4
F. 2 and 5
8. Select the alkene(s) that could be used to produce 3-bromohexane as the major product of the
following reaction.
C
A. 1 only
B. 2 only
C. 3 only
D. 1 or 2
E. 1 or 3
F. 2 or 3
Exam 2 Form 1 CHE 321 Fall 2016
9.
Predict the product of the following reaction.
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D
10. Choose the major product of the following reaction that utilizes deuterium-labeled borane. B
Exam 2 Form 1 CHE 321 Fall 2016
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11. Using the data shown below, draw the most stable conformation of cis-1-bromo-4methylcyclohexane. 5 pts
12. The following bromination of 2,4-hexadiene using only one equivalent of Br2 will yield two major
products, each with molecular formula C6H10Br2. The two products are constitutional isomers.
One of the products is shown below. Draw the structure of the other major product. Note that
each major product is a mixture of stereoisomers. 5 pts
13. Draw the best representation of the transition state of the following step in H-Br addition to
propene. Make sure to show all partial bonds and partial charges. 5 pts
Exam 2 Form 1 CHE 321 Fall 2016
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14. Reduction of an insect pheromone of unknown structure (C13H24O) gives the alcohol on the right.
Ozonolysis gives the three products at the bottom. Predict the structure of the pheromone. 5 pts
15. Based on the information shown below, determine and draw the structures of compounds A and
B. 10 pts
Exam 2 Form 1 CHE 321 Fall 2016
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16. The compound shown below undergoes an acid catalyzed rearrangement to give a chiral
compound as a mixture of enantiomers. Write a curved arrow mechanism and predict the
product. 10 pts
17. Using the library of synthetic reactions shown below as well as your knowledge of alkene addition
reactions, propose a synthesis of the following compound. All your starting materials must be of
four carbons or less. 10 pts