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Spectroscopy Exam Questions

The document is an exam for Chemistry 441 dated October 14, 2014, consisting of 100 points divided among various questions. It includes tasks such as matching IR spectra to molecules, classifying hydrogens, determining coupling constants, and analyzing mass spectra. Students are required to provide organic structures consistent with given spectra and observations.

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Benjamin Park
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70 views8 pages

Spectroscopy Exam Questions

The document is an exam for Chemistry 441 dated October 14, 2014, consisting of 100 points divided among various questions. It includes tasks such as matching IR spectra to molecules, classifying hydrogens, determining coupling constants, and analyzing mass spectra. Students are required to provide organic structures consistent with given spectra and observations.

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

Exam I Chemistry 441

October 14, 2014


Name______________________

This exam consists of 100 points.

1 18
2 20
3 5
4 15
I agree to complete this exam without 5 10
unauthorized assistance from any person, 6 12
materials, or device. 7 10
8 10
9 10
____________________________________
Signature and Date

total 100

1. (18 pts) Some of the following molecules have their IR spectra below and
on the next page. Match the correct molecule with their correct spectrum
(put the letter of the molecule on the spectrum).

OH OH

A B C D
13
CHO CHO
O

OCH3

E F G H I
O

CH3O CN
J

1
G

2
J

2. (20 pts) Classify each of the hydrogens [shown in bold] as homotopic,


enantiotopic, or diastereotopic. A: dia; B: homo or dia; C: enan; D: homo;
E: dia

Br Br
H H Cl Cl

H H H H
OH H H
A B C D
H

H
E

3. (5 pts) Consider the following molecule. What is the expected 1H-13C


cyclopropyl coupling constant (1JC-H)? (160 Hz)

H H
C
Br Br

Br Br
The 1JC-H coupling constant is observed to decrease upon reaction with KOH
in EtOH and loss of 4 mol HBr. Draw a structure that is consistent with this
observation:

3
4. (15 pts) The following mass spectra were taken on propylbenzene (C) ,
isopropylbenzene (B), and acetophenone (A) (methyl phenyl ketone). Which
mass spectrum belongs to which molecule? May switch A and B for 10 pts

CH3C=O

4
5. (10 pts) Provide an organic structure that is consistent with the following spectra (show
all work for full credit).

5
6. (12 pts) Provide an organic structure that is consistent with the following
spectra (show all work for full credit). [splittings: multiplet, quartet, triplet,
sextet, doublet, triplet]

6
7. (10 pts) Provide a reasonable organic structure that is consistent with
the following spectra (show all work for full credit). [singlet, doublet,
doublet, triplet, pentet, sextet, triplet]

7
8. (10 pts) Provide a reasonable organic structure that is consistent with
the following spectra (show all work for full credit).

6 pts for Me and –OH switch

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