Organic chemistry 2 By: Dr E.

Kowsari

Department of Polymer Engineering And color Technology

INFRARED SPECTROSCOPY

INFRARED SPECTROSCOPY

SOME SIMPLE 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, = -C=N, C=C, benzene, oops, etc.).
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

C 3 H 6O

HINT: Can be made from propyne when treated with aqueous H2SO4 and HgSO4.

1421

1715

1363

Problem 2

C3 H 5 N

HINT: Can be made from ethyl iodide and a good nucleophile in acetone (SN2).

2248

Problem 3

C 3 H 8O

HINT: Made by adding water to propene using 3M H2SO4.

3345

1162 1130

970

Problem 4

C5H10O

HINT: The solution to this one is in the hydrogen deficiency index.

1162 3345 994

Problem 5

C7 H 5 N

HINT: The solution to this one is in the hydrogen deficiency index.

2178

Problem 6

C 8 H 8O

HINT: The solution to this one is in the hydrogen deficiency index.

1686

Problem 7

C 4 H 8O 2

HINT: This one stinks like rancid butter.

1712

Problem 8

C 3 H 4O

HINT: There are two functional groups.

2121

Problem 9

C 7 H 6O

HINT: The two peaks at 2820 and 2738 are the key.

2738 2820

1703

Problem 10

C 8 H 8O 2

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
C8H6

H2SO4/HgSO4 H2O

B
C8H8O

Ni / H2
2 atm

C
C8H10O TsCl

pyridine

Spectra are on the pages that follow.

NaCN C9H13N Ni / H2
2 atm

acetone

C9H9N

A C8 H6

2110

3310

B C 8 H 8O

1686

C8H10O

3353

C9 H 9 N

2243

C9H13N

3374 3293

Thanks for your attention