Exam I Chemistry 441 Key
March 7, 2017
Name______________________
This exam consists of 100 points.
1 12
2 12
3 6
4 12
I agree to complete this exam without 5 12
unauthorized assistance from any person, 6 10
materials, or device. 7 10
8 12
9 10
____________________________________
10 4
Signature and Date
total 100
1. (12 pts) The EI mass spectrum of the following molecule produces three
important peaks at m/z 176, 161, and 147. (C14H18O2, MW = 218). Account
for these three peaks:
1
2. (12 pts) Consider the following (in bold) atoms or groups. Indicate
whether they are homotopic, enantiotopic, or diastereotopic.
H H
CH3 CH3
CH3 CH3
enantiotopic enantiotopic diastereotopic
H H
homotopic
3. (6 pts) The following 13C spectrum was taken on cis-1,4-
dimethylcyclohexane at -60 ˚C where exchange between the two chair
conformations is slow on the chemical shift timescale. The assignment of
resonances is indicated. At +30 ˚C, exchange is now fast. How many 13C
resonances do you now expect at the higher temperature?
2
4. (12 pts) Match the following IR spectra with their correct organic
structures (possible answers are listed on the next page).
3
Possible Answers (there is an extra structure):
5. (12 pts). What are the approximate coupling constants (in Hz) for the
following atoms (in bold) in the molecules shown below:
8-14 Hz
6-8 Hz
125 Hz
(allow 100-145 Hz)
4
6. (10 pts) Provide an organic structure that is consistent with the following spectra (show all work for
full or partial credit).
Trans double bond (3 pts)
Methyl ester (3 pts)
18 Hz coupling Phenyl group (3 pts)
(doublets)
7. (10 pts) Provide an organic structure that is consistent with the following spectra (show all work for
full or partial credit). 1H integration (1:1:1:1:4:3). Patterns: doublet of triplets, doublet of pentets,
overlapped peaks, and triplet
4/10 for any other pentyl fluoride All CH2s except for one methyl
5
8. (12 pts) Provide an organic structure that is consistent with the following spectra (show
all work for full credit).
Ketone: 3 pts
Para methoxy:3 pts
Benzyl: 3 pts
Correct structure: 3 pts
2 2 3
2
6
9. (10 pts) Provide an organic structure that is consistent with the following IR and NMR spectra
(show all work for full or partial credit).
CO2Me
OMe
1
H Integration and coupling information: 1:1:1:3:3:3.
8.39 ppm (weak doublet 4J=1 Hz); 8.09 doublet of doublets (4J=1 Hz and
3
J=7 Hz); 7.03 ppm doublet (3J=7 Hz); all other signals are singlets.
Note: do not worry about the specific regioisomer.
Ketone (3 pts); methyl ester (3 pts); methyoxy group on benzene (3 pts)
1,2,4-substitution pattern (based on small and large couplings) (3 pts)
7
10. (4 pts) Provide an organic structure that is consistent with the following spectra (show all work
for full or partial credit).
PhC=O 2 pts
Cyclopropyl group 2 pts
1
H integration2:1:2:1:2:2
