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Spectroscopy Practice Problem 8

The document is an exam key for Chemistry 441 dated March 1, 2016, consisting of various questions related to mass spectra, molecular structures, and NMR spectroscopy. It includes specific point allocations for each question and requires students to provide structures and explanations based on given spectra. The exam covers topics such as isomeric esters, coupling constants, and hydrogen assignments.

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Benjamin Park
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21 views8 pages

Spectroscopy Practice Problem 8

The document is an exam key for Chemistry 441 dated March 1, 2016, consisting of various questions related to mass spectra, molecular structures, and NMR spectroscopy. It includes specific point allocations for each question and requires students to provide structures and explanations based on given spectra. The exam covers topics such as isomeric esters, coupling constants, and hydrogen assignments.

Uploaded by

Benjamin Park
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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Exam I Chemistry 441 Key

March 1, 2016
Name______________________

This exam consists of 100 points.

1 12
2 8
3 18
4 12
I agree to complete this exam without 5 10
unauthorized assistance from any person, 6 16
materials, or device. 7 10
8 8
9 6
____________________________________
Signature and Date

total 100

1. (12 pts) The EI mass spectra of 3-methyl-2-pentanone and 4-methyl-2-


pentanone are shown below. Unfortunately, the mass spec technician lost the labels
and does not know which is which. Provide the correct structure for each showing
why you made your selection (draw appropriate fragments and show how you arrived
at these fragments).

1
2. (8 pts) Draw three different molecules containing homotopic,
enantiotopic, and diastereotopic hydrogens and draw one molecule with
diastereotopic methyl groups. Be sure and indicate the hydrogen pairs
(methyl pair) that are homotopic, enantiotopic, and diastereotopic.
H H H H H H
Cl
HO2C CO2H HO2C Cl HO2C
Br

H3C CH3
Cl
HO2C
Br

3a. (6 pts) An AMX pattern for a vinyl group is shown below. Label the
appropriate hydrogens in the drawing as A, M, or X.

R H
M
C C
H H X
A

3b. (8 pts) Provide approximate coupling constants for:

3
JAM = 15-22 Hz
3
JAX = 8-14 Hz

3c. (4 pts) What is the approximate 4-bond (meta) 1H-1H coupling in benzene
1-3 Hz

2
4. (12 pts) The following 1H spectra were collected on isomeric esters of
propanoic acid. Draw the correct structure of each ester next to its 1H
spectrum.

Nonet

Triplet
Quartet

3
5. (10 pts) Provide an organic structure that is consistent with the following spectra (show all work
for full or partial credit).

4
6a. (10 pts) Provide an organic structure that is consistent with the following spectra (show
all work for full credit).
6b. (6 pts) Assign the 1H resonances at 7.12, 7.26, and 7.37 ppm to specific hydrogens in
your structure.

5
7. (10 pts) Provide an organic structure that is consistent with the following spectra (show all work
for full or partial credit).

OMe

OMe

6
8. (8 pts) Provide an organic structure that is consistent with the following NMR spectra (show all
work for full or partial credit).

7
9. (10 pts) Provide an organic structure that is consistent with the following spectra (show all work
for full or partial credit).

OH

Br

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