Chem 322 - Final 2021
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Chem 322 - Final
2021
1. (15 points) The spectra below correspond to five of the compounds listed at the bottom. Draw the appropriate compound next to each spectrum. No compound is used more than once.
a)
b)
Br
Cl
|
O
O
Br
Br
Br
2. (24 points) The last page of this exam has spectra for an unknown with the formula C9H11NO. Answer the questions below for this unknown.
a) How many degrees of unsaturation does this
b) In the IR, what does the signal at ~3050 suggest?
c) In the IR, there is no signal between 3400 and 3100. What does this suggest?
d) Does this compound have symmetry?
e) In the 13C NMR, what does the chemical shift of the signal at 190 suggest? Please be specific about what the chemical shift suggests.
f) In the 13C NMR, what does the ORD splitting data for the signal at 190 suggest? Please be specific about what the ORD splitting data suggests.
g) In the 1H NMR, what does the chemical shift of the signal at 7.6 suggest? Please be specific about what the chemical shift suggests.
h) In the 1H NMR, what does the integration of the signal at 7.6 suggest? Please be specific about what the integration suggests.
i) In the 1H NMR, what does the splitting pattern of the signal at 7.6 suggest? Please be specific about what the splitting pattern suggests.
j) Draw the structure for the unknown in the box.
3. (36 points) Predict the major organic product or products for the following. Be sure to indicate stereochemistry where appropriate. "No reaction" may be an answer. Assume each of these is in the most appropriate solvent. Assume kinetic conditions.
O
|
CN |
O
Br2 , FeBr3
|
NH2 |
|
O O
O O O |
O
NH
O
OH
NH2
(±)
|
Br
O O
O O Br |
4. (20 points) Fill in the missing reagents for this multi-step synthesis.
O
Cl
a) |
O |
O
b)
a) O3
b) DMS
O
O
c)
H2CrO4
5. (8 points) Here is the structure of the sugar D-gulose.
OH
HO
H
OH
Decide whether each of these is D-gulose (circle the appropriate answer).
CHO
OH
OH
H
OH
CHO
OH
H
H
OH
HO |
OH
O
OH OH |
OH |
O
OH OH |
OH |
c) D-gulose d) D-gulose
Name
6. (8 points) Predict whether each of these would go with heat or light.
b)
Cl
Cl
7. (6 points) Draw the Highest Occupied orbital of this compound. Assume ground state.
8. (9 points) Assuming each of these is planar, label each compound as aromatic, antiaromatic, or nonaromatic.
H
N
|
|
|
N
H
9. (12 points) Suggest a synthesis to achieve one of these two transformations in two or more steps.
OH
steps
OH
steps
Br
OH
PCC
O
O
a) LDA
b) Br
Zn/Hg
HCl
H2O
O
OH
H2CrO4
O
Br2
FeBr3
Br
10. (12 points) Draw a mechanism for this transformation.
H O
H O
H
H+
H+
O
O
H O
O H
H O
H O
O H
H O
2022-08-12