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6A_Lecture_5_with_ink - Lecture 5 Infrared Spectroscopy...

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Lecture 5
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Infrared Spectroscopy Thin Layer Chromatography Experiment 5 Nuclear Magnetic Resonance
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Overtones Carbonyl compounds exhibit them (C=O stretch) C=O functional groups appear in the 1700 cm -1 range Overtone peak shows up at ~3400 cm -1 Do not confuse this with an alcohol A concentration expt can be done to determine if it is an alcohol or an overtone.
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Overtone of cyclohexanone
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Carbonyl (C=O bond) Notice trend from chart in book Related to bond order Anhydride 1850-1800 Acid Chloride 1815-1770 Ester 1765-1735 Aldehyde 1740-1720 Ketone 1750-1705 Carboxylic Acid 1725-1700 Amide 1700-1640
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Conjugation decreases bond order of C=O
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Ring strain increases bond order Ketone C=O stretch Cyclopropanone 1818 Cyclobutanone 1783 Cyclopentanone 1747 Cyclohexanone 1716 Cycloheptanone 1705
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1. Always look at the structures first 2. Find different functional groups between them 3. Find spectra that contain those unique functional group stretches 4. If functional groups and stretches are similar, look for ring strain or conjugation
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