Eight simple steps to the interpretation of IR spectra.

First of all, read the IR material presented in the book (Unit 31) and given in lecture and familiarize yourself with the subject, then follow these simple steps: Draw the molecule. Identify all the functional groups in the molecule (aromatic, alkene, alcohol, ketone, ester, etc.) Ignore alkanes (methyl and methylene groups). In identifying the functional groups be as specific as Table 31.2 is. For example, the table makes a distinction between aliphatic and aromatic esters (R-COOR and Ar-COOR). In Table 31.2, look for all the vibrations for the functional groups in your moledule. Make a list with their frequencies (in cm-1) and assignments. The assignment is given on the third column of Table 31.2 (example: st C=O; st O-H, d N-H, etc; st stands for stretching and d for deformation or bending). If Table 31.2 gives you an option between dimer and monomer or between free and associated (they refer to the degree of self association through Hbonds) use the dimer or the associated values (under the conditions used to run IR spectra, most molecules that can form H-bonds will; they are associated.) Ignore any vibration that takes place between 1000 and 1500 cm-1 (fingerprint region) unless instructed to do otherwise. Match up the vibrations from the list (step 3) with the bands found in your own IR or/and the IR of the same molecule shown in the book. Oftentimes the IR in the book has bands indicated with frequency values. This is not and indication of the importance of the band. Sometimes important bands may lack frequency markers, other times unimportant bands may have them. Keep in mind that the frequencies of the vibrations may have an error of up to 15 cm-1. Ignore nujol bands that may be present in the IRs. Nujol is used as a solvent to obtain the IR of solids. The IR of pure nujol is shown on p. 683 of the lab book. Present your analysis in a table format with five columns such as the one shown below. One of the columns should indicate the name of the functional group the band belongs to (be as specific as Table 31.2 allows you; example: trans alkene; aliphatic aldehyde; aromatic ester, etc.)

If you get separated from your Table 31.2 handout, keep in mind that it is available in the lab book on p. 686.

Expected frequency From Table 31.2

Assignment (st C=O; d N-H,

etc., from table 31.2)

Functional group

Observed frequency (from your own IR, if available)

Literature frequency (from the IR in the book, if available)

Example. Interpretation of the IR (from the literature, the book) of o-chlorobenzaldehyde.

wavenumber (cm - 1 )
4000 3500 3000 2500 2000 1500 1000 500

120 100
% Transmittance

80 60 40 20 0
o-chlorobenzaldehyde (vapor)
1695 2868 2753 3070

Note: vapor means that the IR was obtained in the vapor state, no solvent was used.

Structure:
O H

Cl

o-chlorobenzaldehyde

Functional groups:
aromatic ring, ortho disubstituted aldehyde (aromatic) aryl halide Assignment (st C=O; d N-H, etc., from table 31.2) C-H st C-C st C-H d out-of-plane C-H st and C-H d overtone (Fermi resonance) C=O st C-Cl st Functional group Observed frequency (from your own IR, if available) Literature frequency (from the IR in the book, if available) 3070 1600 * 760 2868 and 2753 1695 800 *

Expected frequency From Table 31.2 3020-3080 1580-1630 730-770 2720 and 2820 1700 <600-840

aromatic phenyl ring 1,2-disubst. arom. ring aldehyde aromatic aldehyde aryl halide

Notice that two bands (the ones with asterisks) had no frequency markers on the spectrum. Their values were estimated from the x-axis of the spectrum. If you had your own IR of o-chlorobenzaldehyde, youd add the observed frequency values on the fourth column.

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