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1315
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Dec 6, 2023
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HW #5, page 1 of 4
CHEM 1315 – Homework Set #5
(20 points)
Due:
3:30 pm, Thursday, Nov. 16
th
, 2023
Reading
for this homework set:
Klein volume 2, chapters 2 and 3, class notes lectures 19, 20 & 21.
Key concepts:
Light-matter interactions, UV-Vis Spectroscopy, Combustion Analysis, IR
Spectroscopy, Mass Spectrometry, NMR Spectroscopy
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1. (3 pts) How many signals would you expect to see in the
1
H &
13
C NMR spectra of each compound
below, (i.e. how many chemically distinct H & C atoms are present in each molecule?) (.5 pt each)
# H signals:
___
____
____
# C signals:
___
____
____
Name:
HW #5, page 2 of 4
2. (2 pts) Combustion analysis on a molecule yields the following data: 54.53 wt% C, 9.15 wt% H,
and 36.32 wt% O. Mass spectrometry data shows the M•+ peak has an m/z of 88. What is the
chemical formula of the molecule? Show your work.
3. (3 points) Below are pairs of molecules. You are given a sample that contains one of them, but
you don’t know which.
Using FTIR, describe a spectral feature, or combination of features, that can
be used to unambiguously identify which of the two compounds is the sample (note: be specific
–
e.g. do not say “I’d expect the spectrum to have a C=O peak if it’s the molecule on the right”; also
list the approximate cm
-1
where you’d expect to find
this peak) (1.5 pts each):
a)
b)
HW #5, page 3 of 4
4. (3 points) Below are pairs of molecules. You are given a sample that contains one of them, but
you don’t know which.
Using 1H NMR or 13C NMR, describe a spectral feature, or combination of
features, that can be used to unambiguously identify which of the two compounds is the sample
(note: be specific
–
e.g.
do not say “the splitting pattern is different”; quantify how many peaks or
approximate ppm you’d expect)
(1.5 pts each)
:
a)
b)
5. A dye molecule is dissolved in a solvent, placed in
a cuvette, and its UV-vis spectrum is shown at right.
a) (1 pt) What energy of light in eV is being absorbed
at 610 nm? Show your work.
b) (1 pt) Given the molar absorptivity of the molecule
is 122,000 M
-1
cm
-1
and the cuvette is 1 cm wide, what
is the concentration of your sample? Show your work.
a)
b)
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HW #5, page 4 of 4
6. (7 points) A molecule
has the formula:
C
9
H
10
O
2
. Using the spectra below, answer the following:
a) Calculate the degrees of unsaturation: ____ (1 pt)
b) How many non-equivalent carbons are there? ____ (1 pt)
c) In the
1
H NMR spectrum, what structural motif gives rise to peak
a
?
(write the name or draw
the motif)
_______ (1 pts)
d) In the
13
C NMR spectrum, circle the peak that corresponds to the structural motif identified
above in part c) (1 pt)
e) In the FTIR
spectrum, circle
two
peaks > 1500 cm
-1
that correspond to the structural motif
identified above in part c) (1 pt)
f)
In the
1
H NMR spectrum, how many neighboring H’s does peak
d
have? ______ (1 pt)
g) Draw the molecule (1 pts)
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