CHM 2020 Exam 3
Name _________________________________________
Date ___________________
Part I. Functional group review.
Each question is worth two (2) points each. There is no partial credit. (12 points)
1. Match the given structures to appropriate functional group represented by writing the matching
letter in the space provided under each structure.
O
O
NH2
O
N
H
HN
O
C
N
Cl
A. Acid chloride
B. Acetal
C. Aldehyde
D. Alcohol
E. Amide
F. Amine
G. Anhydride
H. Enamine
I. Ester
J. Imine
K. Ketone
L. Lactam
M. Lactone
N. Nitrile
Page 1 of 11
CHM 2020 Exam 3
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.
NO 2
A
+
NH2
N N
B
Cl
A
C
Br
-
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.
A
Br
N3
B
NH2
C
NH
O
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
NH2
NH2
C
B
N
N
H
A
B
C
Page 2 of 11
CHM 2020 Exam 3
Part III. Reaction Review.
Each question is worth three (3) points each. There is no partial credit. (27 points)
5. Draw the major organic product(s) formed in the following reaction transformations. Show
stereochemistry if applicable.
1. KOH
2. 1-bromohexane
O
NH
3. NaOH, H2O
O
O
O
O
O
+
O
NaOEt
O
EtOH
1. Br2, AcOH
2. pyridine
O
1. excess Br2, KOH
2. H2O
Page 3 of 11
CHM 2020 Exam 3
NH2
1. NaNO2, HCl
2. H2O
O
O
O
1. NaOEt
O
O
2. H2O, HCl
1. LDA, -78 °C
2. CH3CH2CH2Br
O
O
NaOEt
EtOH
NH2
1. Excess CH3I
2. Ag2O, H2O
3. heat
Page 4 of 11
CHM 2020 Exam 3
Part IV. Synthesis.
Each question is worth five (5) points each. (10 points)
6. Determine the product, E, of the following reaction sequence. Draw the structure of intermediates A
– D to receive partial credit. Please label each intermediate with the appropriate letter. (10 points)
O
1. NaBH4
H
A
SOCl2
NaCN
B
C
1. LDA, -78 °C
D
2. CH3CH2Br
2. H2O
1. LiAlH4
E
2. H2O
Cl
Product E
7. Determine the product, D, or the following reaction sequence. Draw the structures of intermediates
A – C to receive partial credit. Please label each intermediate with the appropriate letter. (8 points)
O
1. NaOEt
O
2.
O
A
1. NaOEt
2. CH3CH2Br
B
H3O+, heat
C
1. LDA
D
2.
Br
O
3. H3O+
Product D
Page 5 of 11
CHM 2020 Exam 3
Part V. Spectroscopy.
8. Match the correct constitutional isomer with the appropriate 1H NMR spectra below. Write the
letter of the spectra A, B, C, or D in the box located below each compound. (12 points)
H
N
NH2
N
N
H
Spectra A
Spectra B
Page 6 of 11
CHM 2020 Exam 3
Spectra C
Spectra D
Page 7 of 11
CHM 2020 Exam 3
Part VI. Reactions Conditions Match-up.
Each question is worth two (2) points each. There is no partial credit. (8 points)
9. Determine the correct reaction conditions to produce B from the starting material, A. Place an X
over the incorrect reaction conditions.
O
O
O
LDA, -78 °C
NaOEt, 25 °C
Br
B
B
A
10. Draw the expected product from the selected incorrect reaction conditions.
11. Determine the correct reaction conditions to produce C from the starting material, A. Place an X
over the incorrect base and reaction conditions.
O
O
O
LDA, -78 °C
NaOEt, 25 °C
Br
C
A
C
12. Draw the expected product using the selected incorrect reaction conditions.
Page 8 of 11
CHM 2020 Exam 3
Part VII. Concept Review.
Each question is worth two (2.5) points each. There is no partial credit. (5 points)
13. Circle the thermodynamic enolate of 2-methylcyclohexanone?
O
-
O
-
O
-
O
-
14. Circle the carbonyl compounds that do not undergo self- aldol reactions with treated with NaOH in
H2O?
O
O
O
H
H
O
O
O
H
Page 9 of 11
CHM 2020 Exam 3
Part VII. Retrosynthesis.
Each question is worth four (4) points each. (8 points)
15. Draw the reactants used to produce the following compound from a crossed Claisen reaction.
O
O
KOH
H2O
16. Draw the reactants needed to prepare the following compound using a Robinson Annulation.
KOH
O
H2O
Page 10 of 11
CHM 2020 Exam 3
Page 11 of 11