Answer Key for IR assignment Winter 2003

Spectrum 1: Isobutylamine (liquid)

Frequency Assignment
3372, 3297 n(NH2)
2871, 2955 nCH, sp3)
1602 d(NH2)
1470 d (CH3, bend)
1387, 1366 d (-C(CH3)2, stretch)


Spectrum 2: N-(3-bromopropyl)-phthalimide (solid)
Frequency Assignment
3025 n(CH, sp2, aromatic)
2927 n(CH, sp3)
1765, 1702 n(C=O, 'anhydride')
~1603, 1462 n(C=C, aromatic)
723 oop, ortho-subst.


Spectrum 3: o,o'-biphenol (solid)
Frequency Assignment
3200-3400, br n(OH), alcohol
1609, 1484 n(C=C, aromatic)
1226 n(CO, stretch)
746 oop, ortho-subst.


Spectrum 4: Trans-cinnamic acid (solid)
Frequency Assignment
2500-3400, br n(OH, acid)
1682 n(C=O)
1629 n(C=C, alkene)
979 oop, trans alkene


Spectrum 5: Ethyl-isobutyrate (liquid)
Frequency Assignment
2878-2979 n(CH, sp3)
1735 n(C=O, ester)
1472, 1385 d (CH2, CH3, bend)
1157, 1078 n(COC, stretch)


Spectrum 6: n-Heptyl cyanide (liquid)
Frequency Assignment
2858-2956 n(CH, sp3)
2247 n(C=N, nitrile)
1466, 1379 d (CH2, CH3, bend)
724 d ((CH2)4, rocking)


Spectrum 7: Progargyl alcohol (liquid)
Frequency Assignment
3200-2500 n(OH, alcohol)
3293 n(CH, sp)
2873, 2928 n(CH, sp3)
2120 n (C=C, alkyne)
1028 n(CO, stretch)


Spectrum 8: o-Nitro benzaldehyde (solid)
Frequency Assignment
3104 n(CH, sp2)
2867 n(CH, aldehyde)
1694 n(C=O)
1518, 1353 n (NO2, stretch)


Spectrum 9: 2-Carene (liquid)
Frequency Assignment
2729-2996 n(CH, sp3)
1665 n(C=C)
1449, 1373 d (CH2, CH3, bend)
827 oop, tri-substituted


Spectrum 10: [(cis)-endo]borneol (solid)
Frequency Assignment
3200-3400 n(OH)
2878-2952 n(CH, sp3)
1454, 1387 d (CH2, CH3, bend)
1055 n(CO, stretch)


General comments:

1. The average grade for the assignment is 32 points (out of 40). If you scored significantly less than 30 points, I would advise you to see your TA or the instructor to seek some help and get a better insight on IR spectroscopy.

2. One of the most common mistakes was not to analyze the n(C-H) region correctly to determine what type of compound (alkane, alkene, aromatic, or mixed) is present.

3. The n(OH) peaks for acids and alcohols look very different and can be easily identified by looking at them (see reader page 103).

4.Carbonyl peaks can be shifted to lower wavenumbers when the carbonyl function is conjugated to a p-system e.g. double bond or aromatic ring.

5. Nitro groups show two intense peaks in the IR spectrum: one between 1300-1400 cm-1for the symmetric stretching mode, the other one between 1500-1600 cm-1 for the asymmetric stretching mode

6. The presence of two peaks in the carbonyl range (1630-1850 cm-1) indicates either the presence of an "anhydride type" of function or two different carbonyl functions.

7. Peaks due to amine, alkyne or alcohol functions are very different in appearance. Alkyne peaks (CH stretch) are very sharp and fairly intensedue to the isolated motion. Amine peaks are usually a little broader and less intense. The presence of two peaks suggests a primary amine (NH2) while secondary amines show only one peak in this range. Alcohols (OH-stretch) usually show a rounded peak in this area.

8. A lot of noise of the left side of the spectrum usually indicates that the spectrum was acquired as a KBr pellet, meaning that the compound is a solid.