CHM 2020 Exam 2
Name _________________________________________
Date ___________________
Part I. Functional group review.
Each question is worth two (2) points each. There is no partial credit. (12 pts)
1. Match the given structures to appropriate functional group represented by writing the matching
letter in the space provided under each structure.
O
HN
O
O
O
NH
O
O
O
A. Acid chloride
B. Acetal
C. Aldehyde
D. Alcohol
E. Amide
F. Amine
G. Anhydride
N
H. Enamine
I. Ester
J. Imine
K. Ketone
L. Lactam
M. Lactone
N. Nitrile
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CHM 2020 Exam 2
Part II. Multi-step synthesis reactions.
Each reaction transformation is worth two (2) points each. There is no partial credit. (18 pts)
2. Use the space provided below to write the chemical formula or draw the structure of the
reagent(s) used to complete each reaction transformation.
O
O
A
OH
N
O
Cl
B
O
C
O
N
NH2
N
A
N
B
C
3. Use the space provided below to write the chemical formula or draw the structure of the
reagent(s) used to complete each reaction transformation.
O
A
Br
O
B
OH
C
NH2
NH2
A
B
C
4. Use the space provided below to write the chemical formula or draw the structure of the
reagent(s) used to complete each reaction transformation.
O
A
A
O
OH
B
O
Br
B
C
C
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CHM 2020 Exam 2
Part III. Reaction Review.
Each question is worth two (2) points each. There is no partial credit. (18 pts)
5. Draw the major product(s) formed in the following reaction transformations.
O
1. H3O+, SH
SH
2. Raney Ni
O
O
excess H2
O
O
Pt
O
1. NaBH4
O
2. H2O
O
CrO3
H
H2SO4, H2O
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CHM 2020 Exam 2
O
1. (CH3CH2CH2)2CuLi
2. H2O
1. O3
2. CH3SCH3 or DMS
O
CH3NH, DCC
OH
O
HO
H2SO4
OH
1. CH3CH2CH2Li
N
2. H2O
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CHM 2020 Exam 2
Part IV. Mechanism.
6. Draw a stepwise mechanism for the following reaction. (14 points)
O
O
O
cat. TsOH, H2O
+
HO
OH
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CHM 2020 Exam 2
Part V. Spectroscopy and Synthesis.
7. Draw product, E, of the following reaction sequence. Use the corresponding 1H NMR spectrum
to confirm if the product is ortho or para substituted. Draw and label products A thru E to
receive partial credit (10 points)
O
Br CH3COCl
A
AlCl3
OH
HO
B
H3O+
Mg
C
H
D
H3O+
PCC
E
Product F
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F
CHM 2020 Exam 2
Part VI. Spectroscopy.
No partial credit.
8. Match the correct constitutional isomer with the appropriate 1H NMR spectra below. Write the
name of the spectra A, B, C, or D in the box located below each compound. (12 points)
O
H
O
H
O
H
O
H
Spectra A
Spectra B
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CHM 2020 Exam 2
Spectra C
Spectra D
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CHM 2020 Exam 2
9. Use the following 1H and 13C NMR spectra to determine the correct constitutional amide.
Please circle your answer. (6 points)
O
N
O
O
N
H2N
H
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CHM 2020 Exam 2
Part VI. Reagent Review.
Please circle one reagent from the options given to answer the questions provided below.
Each question is worth 2 points. No partial credit. (10 points)
10. Which reagent should you use to convert an aldehyde or ketone into an alkene?
Gilman reagent
Tollens reagent
Wittig reagent
11. Which reagent should you use to reduce an ester to an aldehyde?
DIBALH
LiAlH4
NaBH4
12. Which reagent should you use to convert an amide into a nitrile?
H3O+
LiAlH4
SOCl2
13. Which reagent should you use to reduce the alkene only in an α, β – unsaturated compound?
(1 equiv.) H2, Pt
NaBH4
Excess H2, Pt
14. Which reagent is used to oxidize an aldehyde to a carboxylic acid?
KMnO4
Ag2O, NH4OH
PCC
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CHM 2020 Exam 2
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CHM 2020 Exam 2
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