Organic Chemistry: Spectroscopy

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1. infrared measures molecular vibrations of 19. UV spectroscopy involves passing ultraviolet light
spectroscopy characteristic functional groups through a chemical sample and
2. alkanes IR C−H 2800-3000 cm⁻¹ plotting absorbance vs. wavelength
wavenumber most useful for studying compounds
containing double bonds and
3. alkanes IR C−C 1200 cm⁻¹
heteroatoms with lone pairs
wavenumber
20. ¹H-NMR a form of nuclear magnetic
4. alkenes IR =C−H 3080-3140 cm⁻¹
resonance
wavenumber
21. chemical shifts (δ) are downfield from TMS
5. alkenes IR C=C 1645 cm⁻¹
wavenumber 22. RCH₃ chemical shift 0.9 ppm

6. alkynes IR C≡C 2200 cm⁻¹ 23. RCH₂ chemical shift 1.25 ppm
wavenumber 24. R₃CH chemical shift 1.5 ppm
7. alkynes IR ≡C−H 3300 cm⁻¹ 25. −CH=CH chemical 4.6-6 ppm
wavenumber shift
8. aromatic IR C−H 2900-3100 cm⁻¹ 26. −C≡CH chemical shift 2-3 ppm
wavenumber 27. Ar-H chemical shift 6-8.5 ppm
9. aromatic IR C−C 1475-1625 cm⁻¹ 28. −CHX chemical shift 2-4.5 ppm
wavenumber
29. −CHOH/−CHOR 3.4-4 ppm
10. alcohols IR O−H 3100-3500 cm⁻¹ chemical shift
wavenumber broad
30. RCHO chemical shift 9-10 ppm
11. ethers IR C−O 1050-1150 cm⁻¹
31. RCHCO− chemical 2-2.5 ppm
wavenumber
shift
12. aldehydes IR 2700-2900 cm⁻¹
32. −CHCOOH/−CHCOOR 2-2.6 ppm
(O)C−H
chemical shift
wavenumber
33. −CHOH−CH₂OH 1-5.5
13. aldehydes IR C=O 1700-1750 cm⁻¹
chemical shift
wavenumber
34. ArOH chemical shift 4-12
14. ketones IR C=O 1700-1750 cm⁻¹
wavenumber 35. −COOH chemical 10.5-12
shift
15. carboxylic acids 1700-1750 cm⁻¹
IR C=O 36. −NH₂ chemical shift 1-5
wavenumber 37. ¹H NMR guide
16. carboxylic acids 2800-3200 cm⁻¹
IR O−H broad
wavenumber
17. amine IR N−H 3100-3500 cm⁻¹
wavenumber sharp
18. IR spectroscopy
guide

38. when analyzing an 1. types of protons

NMR spectrum, look 2. position of peaks
for 3. integration of peaks
4. splitting
39. types of protons correspond to the number of peaks
seen in the spectrum
40. position of the further left-shifted (downfield) the peak, the more deshielded the proton
peaks usually this corresponds to more electron-withdrawing groups
41. integration of the larger the integration, the more protons contained under the peak
peaks
42. splitting hydrogens on adjacent carbons will split a peak into n + 1 subpeaks, where n is the number of
hydrogens on the adjacent carbon