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Instructions This exam will be closed book. No notes, books, calculators, or molecular models will be allowed. The exam will be comprised of two distinct parts: Part I will consist of a series of multiple choice questions. Your answers to these questions must be submitted on a Scantron bubble sheet. The answer sheet will be provided for you, but you will need your own #2 pencil(s). Only answers marked on the bubble sheet will be graded. Answers to Part I questions marked on the exam itself cannot not be graded. No re-grades will be possible on Part I of the exam. Part II consists of questions for which you will need to write out your answers, using structures and/or words. This part of the exam will be hand-graded. Answers for the Part II questions that are written in pencil will not be eligible for re-grades. Answers written in pencil with ink overlay will not be eligible for re-grades. If you use a pen to answer the Part II questions, only blue or black ink is acceptable. Answers written in red ink cannot be graded. 1. You must have your valid UT ID card (or other government-issued ID) with you. You will need to show it to the proctors when you turn in your exam. 2. Chapter 4 of the Universitys General Information catalog outlines this universitys policies regarding exams, as well as other quizzes administered during the semester. Specifically, students are expected to remain in the exam room until a test is completed. These policies will be strictly enforced, with no exceptions. You may not leave the room for any reason until you are ready to turn in your exam. If you wish to leave the room, you will need to turn in your exam to the proctors, and you will not be allowed to return. Please, plan accordingly by using the rest room before the exam starts.

CH 328 N Exam I
Question 1 2 3 4 5 6 Section II Section I Raw Total Value 10 20 15 15 15 15 90 60 150 Score

Grade

UTID: ________________________

September 2013

CH 328N-Exam 1
Objective Section Identify the choice that best completes the statement or answers the question. Only one choice is correct; be sure to carefully bubble your answer on the scantron sheet. (4 pts ea.; 60 pts this section)

1. What is the x-axis of a mass spectrum? a. mass/energy b. mass/charge c. charge d. mass 2. Which C4H9Br compound gives a triplet at approximately 3.5 ppm in the 1H NMR spectrum?

a. b. c. d.

1 2 3 4

3. What is the hydrogen deficiency index for a compound with a molecular formula of C 10H16O2? a. 1 b. 2 c. 3 d. 4 4. Which feature in the 1H NMR spectrum provides information about the relative number of each type of
proton in a compound? a. number of signals b. splitting c. chemical shift d. integral

5. What reactive intermediates are involved in the following reaction?

a. b. c. d.

the trichloromethyl anion (Cl 3C: ) and dichlorocarbene (Cl 2C:) the cyclohexyl carbocation the cyclic chloronium ion derived from cyclohexene the trichloromethyl cation (Cl 3C+)

6. Which of the following processes takes place upon absorption of infrared radiation? a. electron spin flip b. bond vibration c. electron excitation d. nuclear spin flip 7. Which feature in the 1H NMR spectrum provides information about the number of neighboring protons
of each proton in the compound? a. integral b. chemical shift c. multiplicity d. number of signals

8. Which of the following sets of molecular ions does an alkyl bromide possess? a. b. c. d.
two molecular ions in a 1:1 ratio separated by two mass units two molecular ions in a 3:1 ratio separated by two mass units three molecular ions in a 1:2:1 ratio separated by two mass units two molecular ions in a 2:1 ratio separated by two mass units

9. Which of the following bonds has the most ionic character? a. CHg b. CAl c. CMg d. CZn 10. Which of the following sets of molecular ions does an alkyl chloride possess? a. b. c. d.
two molecular ions in a 3:1 ratio separated by two mass units two molecular ions in a 1:1 ratio separated by two mass units three molecular ions in a 1:2:1 ratio separated by two mass units two molecular ions in a 2:1 ratio separated by two mass units

11. Which of the following compounds gives an infrared spectrum with peaks at 3000-3500 cm 1 and
~1750 cm1?

a. b. c. d.

1 2 3 4

12. Which of the following bonds gives rise to a strong, broad, absorbance at approximately 3200-3650 cm 1
in the infrared spectrum? a. C=O b. CH c. C=C d. OH

13. What is the y-axis of a mass spectrum? a. abundance b. field strength c. mass d. energy 14. Which of the following alcohols can be prepared from a Grignard reagent and ethylene oxide?

a. b. c. d.

only 1 only 1 and 2 only 1, 2 and 3 1, 2, 3 and 4

15. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

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CH 328N-Exam 1 Answer Section

MULTIPLE CHOICE 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. ANS: ANS: ANS: ANS: ANS: ANS: ANS: ANS: ANS: ANS: ANS: ANS: ANS: ANS: ANS: B A C D A B C A C A C D A B A PTS: PTS: PTS: PTS: PTS: PTS: PTS: PTS: PTS: PTS: PTS: PTS: PTS: PTS: PTS: 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4

CH 328 N EXAM #1
PART 2: Free Style Answer Format

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KEY

(90 pts in this section)

1) There are four constitutional isomers of dichloropropane. The NMRs of 3 of these are shown below. Match each isomer with its NMR and provide an interpretation of each spectrum. (i.e. draw the structure on the NMR and label protons, with their splitting.) (10 pts)

a, singlet Cl C H3C a CH3 a Cl

PPM

4 a

Cl

b, pentet H2 Cl C C C b H2 H2 a, triplet a, triplet 2

2 PPM

CH 328 N EXAM #1

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2) Provide either the reagents or the product(s) for the following reactions. This is not a mechanism question-simply write the answers in the boxes. (5 pts per structure) O OH 1) PhMgBr 2) HCl/H2O Ph

OH 1) CH3CH2CH2Li H 2) HCl/H2O

CH3

CH2I2; ZnCu

CH3

H3C C Cl CuLi 2 CH2 CH2

CH 328 N EXAM #1

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Unknowns: The molecular formula, IR & NMR are provided for the following unknown compounds. For each problem, provide the structural information from the IR & NMR and propose a structure for the unknown.

3) Unknown 1 (the compound has a formula of C5H12O)

IR indicates (just provide the functional group(s):

Draw the structure & label the protons using the a,b,c labeling method.

CH 328 N EXAM #1

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4) Unknown 2 (the compound has a formula of C4H8O2)

IR indicates (just provide the functional group(s):

See next page for expanded NMR of Unknown 2

CH 328 N EXAM #1

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Unknown 2: expanded NMR

12 peaks

Draw the structure & label the protons using the a,b,c labeling method.

CH 328 N EXAM #1

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5) Unknown 3 (the compound has a formula of C6H12O2)

IR indicates (just provide the functional group(s):

Draw the structure & label the protons using the a,b,c labeling method.

10

CH 328 N EXAM #1

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6) Unknown 4 (the compound has a formula of C5H11Br)

IR indicates (just provide the functional group(s):

Draw the structure & label the protons using the a,b,c labeling method.

END OF EXAM SECTION

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