Chem 322 - Final exam 2020
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Chem 322 - Final exam
2020
1) (16 points) Predict the major organic product or products for each of these. Assume kinetic conditions and the most appropriate solvent for each.
H3CO a) |
|
|
O |
heat |
O O
H+, excess H2O
a) LiAlH4
b) H+
a) LDA
b)
Br
2. (3 points) Draw the highest occupied and lowest unoccupied molecular orbitals of this compound.
Lowest Unoccupied
Highest Occupied
3. (9 points) Suggest a multi-step synthesis to achieve the following transfomation.
steps
O
Br
4. (10 points) The IR, 13C NMR and 1H NMR for a compound with the formula C10H10O3 are on
page 4.
a. How many degrees of unsaturation does this compound have?
b. What is one type of bond that is in this compound based on the IR spectrum?
c. What signal in the IR led to your response to question b?
d. In the 13C NMR, what does the ORD splitting information
for the signal at 55 indicate? Please be specific about the splitting.
e. In the 1 H NMR, what does the splitting pattern for the signal at
6.0 indicate? Please be specific about the splitting.
f. Draw the unknown compound.
g. Draw the fragment that gives the base peak in
the mass spectrum.
5. (3 points) Draw a Fischer projection for this sugar.
OH OH
HO
OH
OH O
6. (9 points) Suggest a mechanism for this transformation.
O
Br
O
O
N
OH
4. MS, IR, 13C NMR, and 1 H NMR spectra for question 4.
This is a blank page in case you need extra space for any of the problems. You do not have to turn this page in if there is nothing you want graded on it. If you do use this page, please clearly write on that question to please look to the extra page.
1) (16 points) Predict the major organic product or products for each of these. Assume kinetic conditions and the most appropriate solvent for each.
(±) H3CO
O |
O OH
|
|
|
2. (3 points) Draw the highest occupied and lowest unoccupied molecular orbitals of this compound.
Lowest Unoccupied
Highest Occupied
3. (9 points) Suggest a multi-step synthesis to achieve the following transfomation.
steps
O
Br
|
|
O
OH
|
|
O
Cl
|
|
O
|
|
O
|
Br |
a) O3 H2CrO4 SOCl2 AlCl3 Br2
b) DMS FeBr3
4. (10 points) The IR, 13C NMR and 1H NMR for a compound with the formula C10H10O3 are on
page 4.
a. How many degrees of unsaturation does this compound have?
b. What is one type of bond that is in this compound based on the IR spectrum? multiple answers for b and c:
c. What signal in the IR led to your response to question b?
6 |
CO2H - 3300-2500
sp2CH - 3100
sp3CH - 2900
CO double bond - 1700
CC double bond - 1600
d. In the 13C NMR, what does the ORD splitting information for the signal at 55 indicate? Please be specific about the splitting. 3 H's on this C (CH3)
e. In the 1 H NMR, what does the splitting pattern for the signal at
6.0 indicate? Please be specific about the splitting. 1 CH next door to this H
f. Draw the unknown compound. O
OH
OCH3
g. Draw the fragment that gives the base peak in
the mass spectrum.
OH
5. (3 points) Draw a Fischer projection for this sugar.
CH OH
OH OH
HO
OH
HO H
OH O
HOH
CH2OH
6. (9 points) Suggest a mechanism for this transformation.
O
Br
O
O
N
OH
O
Br
O
N O H
H
N
H
O
O
N
O
N
H
O
O
N
O
2022-08-12