ASSIGNMENT 1

IR PROBLEMS
 These can be solved using infrared and
an index of hydrogen deficiency.

SOME SIMPLE IR PROBLEMS

Assign all the peaks that you can (that is,

label them right on the spectrum) with the type
of bond responsible for the absorption: C=O,
C-H, -CH2- or -CH3 bending, N-H, O-H, C-O,
= benzene, oops, etc.).
-C=N, C=C,

Unless otherwise noted, a bond designation implies

stretching - bending and oops must be specifically
noted. For instance, “C=O” or “C-H” imply stretching.
Problem 1 HINT: Can be made from propyne
when treated with aqueous H2SO4
C 3H6O and HgSO4.

1421

1715 1363
Problem 2 HINT: Can be made from
ethyl iodide and a good
C 3H5N nucleophile in acetone (SN2).

2248
Problem 3 HINT: Made by adding
water to propene using
C 3H8O 3M H2SO4.

1162
3345 1130 970
Problem 4 HINT: The solution to this
one is in the hydrogen
C5H10O deficiency index.

1162
3345 994
Problem 5 HINT: The solution to this
one is in the hydrogen
C 7H5N deficiency index.

2178
Problem 6 HINT: The solution to this
one is in the hydrogen
C 8H8O deficiency index.

1686
Problem 7 HINT: This one stinks
like rancid butter.
C4H8O2

1712
Problem 8 HINT: There are two
functional groups.
C 3 H4 O

2121
Problem 9
HINT: The two peaks at
C 7 H6 O 2820 and 2738 are the key.

2738
2820

1703
Problem 10

C8H8O2

1112
1724 1279
PRACTICAL APPLICATION

This next problem is a little more

difficult, requiring both infrared
and a knowledge of reactions.
Problem 11
As a project, Mary was given an unknown compound A, and told to perform the
reactions listed below. At the end of each reaction step she was told to submit
the major product for microanalysis, in order to obtain the molecular formula,
and to also determine its infrared spectrum. The structure of each compound
was to be identified. Can you help her solve the structures and pass this class?

A B C
H2SO4/HgSO4 Ni / H2
C8H6 C8H8O 2 atm
C8H10O
H2O TsCl
pyridine
NaCN
Spectra are on the acetone
pages that follow. Ni / H2
C9H13N C9H9N
2 atm

E D
A C 8 H6

2110

3310
B C 8 H8 O

1686
C C8H10O

3353
D C 9 H9 N

2243
E C9H13N

3374
3293