CHM 2020 Exam 1
Name ________________________________________________
Date ______________
Part 1: Each question is worth four (4) points. No partial credit.
1. Classify the number of 1H NMR peaks you expect from the following compounds?
2. Classify each compound as aromatic, antiaromatic, and nonaromatic?
3. How many 13C NMR peaks do you expect the following compound to exhibit?
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CHM 2020 Exam 1
4. Classify the type of radical intermediate for each molecule as primary, secondary, or tertiary.
5. Classify each of the following dienes as conjugated, cumulative, or isolated double bonds?
6. Classify the substituent on each aromatic compound as an ortho/para or meta director?
7. Classify number of 13C peaks you expect for the following compounds?
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CHM 2020 Exam 1
Part II. Draw the missing product, reactant, or reagent. Each question is worth 2 points.
No partial credit.
8. Draw the product(s) of the following reaction.
∆
9. Write the missing reagent(s) necessary to produce the product in the following reaction.
10. Draw the product(s) of the following reaction.
11. Write the missing reagent(s) necessary to produce the product in the following reaction.
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CHM 2020 Exam 1
11. Draw the product(s) of the following reaction.
12. Draw the product(s) of the following reaction.
13. Draw the product(s) of the following reaction.
14. Provide the missing reagent(s) necessary to produce the product in the following reaction.
15. Draw the product(s) of the following reaction.
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CHM 2020 Exam 1
Part III. Write the name of the indicated functional group in the space provided.
Each question is worth 4 points. No partial credit.
16. Identify the four functional groups in the following molecule.
A
A.
C
B.
B
C.
D
D.
17. Identify the four functional groups in the following molecule.
G
E.
E
H
F.
G.
F
H.
18. Identify the four functional groups in the following molecule.
K
J
I.
J.
K.
I
L
L.
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CHM 2020 Exam 1
Part VI: Reaction mechanisms.
Each question is worth 6 points.
17. Show the mechanism for the following radical reaction.
hν
18. Draw the mechanism for the following reaction.
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CHM 2020 Exam 1
Part V. Synthesis. No partial credit.
19. Provide the reagent(s) in the following synthesis reaction(s). (4 points)
20. Provide the reagent(s) in the following synthesis reaction(s). (6 points)
21. Provide the reagent(s) in the following synthesis reaction(s). (4 points)
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CHM 2020 Exam 1
Part VII: Spectroscopy. No partial credit.
22. Circle the constitutional isomer that matches the spectra below. (3 points)
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CHM 2020 Exam 1
23. Determine the constitutional isomer represented in the 1H NMR spectra below. (2 point)
24. Evaluate the 1H NMR spectra below to determine if it is ortho, meta, or para disubstituted
bromobenzene compound. Draw the structure of the product in the box provided below. (5 points)
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CHM 2020 Exam 1
25. Match the correct constitutional isomer with the appropriate 1H NMR spectra below. Write the
name of the spectra in the space provided below each compound. (6 points)
Spectra A
Spectra B
Spectra C
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CHM 2020 Exam 1
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CHM 2020 Exam 1
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