IR SPECTRUM PRACTICE

Question 1. Which of these molecules best corresponds to the IR spectrum below ?

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Question 2. What is the structure of the compound that gives the following infrared and PMR
spectra ?
Question 3. Unknown molecule with molecular formula as given. Which of these molecules is it most
likely to be?

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Question 4. Indicate which one of the following 6 compounds corresoponds to each of the IR spectra
shown below. Indicate the important absorptions that allowed you to make the assignment.
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Question 5. Each of the following IR sprectra (shown below) corresponds to one of the five isomers of C4H8O.
Match the spectrum to the correct structure.
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Question 6. Using the spectra of o –, m –, p – cylene to match the spectrum with appropriate structure.
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Question 7. In each of these problems you are given the IR, NMR, and molecular formula. Using this

information, your task is to determine the structure of the compound.

The best approach for spectroscopy problems is the following steps:

1. Calculate the degree of unsaturation to limit the number of possible structures. Remember, each

degree of unsaturation is a ring or pi bond (likely an alkene or carbonyl). An alkyne has two

degrees of unsaturation (2 pi bonds), and an aromatic ring has four (3 pi bonds plus a ring.)

Although there's no guarantee, if your structure has more than four degrees of unsaturation it's

quite likely to have an aromatic ring.

2. Look at the IR absorption bands at wavenumbers above 1500 cm-1 to determine what functional

groups are likely in the compound. Remember that these functional groups must be consistent

with the degree of unsaturation.

3. Look at the NMR to determine the connectivity of the compound. If you can't figure out the

entire structure at once, it helps to come up with fragments of the molecule that you can stick

together into larger and larger groups until you have the entire structure.

4. Approach this as a puzzle - it can be fun!

a) C5H10O
b) C7H14O
c) C4H10O
d) C6H14O
e) C4H8O2
f) C5H10O2
g) C8H14O3
h) C5H10O
i) C11H14O2
j) C3H6O2
k) C8H8O2
l) C7H9N
m) C5H13N
n) C8H14O
o) C4H9Br
p) C10H14O
q) C13H10O3
r) C8H14
s) C9H13N
t) C9H10