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Proton NMR spectroscopy (uses radio waves to achieve nuclear spin excitation):
Number of different signals = Number of different protons
o Beware of symmetry!
Chemical environments based on chemical shifts
o Aldehyde protons
9-10 ppm
o Alkyl protons
1-1.5 ppm
o Alkene protons
5-6 ppm
o “Aromatic” protons
5.5-8.5 ppm
o Carboxylic acid protons
11-12 ppm
o Protons on carbons attached to EWG (O, N, X)
3.2-4.6 ppm
o Protons alpha to a carbonyl or Alkynes
2-2.5 ppm
Proton coupling:
o Multiplicity prediction based on 3-bond neighbors
o Coupling constants (E vs. Z vs alkyl)
o Beware of Symmetry
Integrations
o Ratios!!, not specific numbers of protons
o Beware of symmetry!
Understand the relationship between electron density, shielding, and chemical shift
Carbon NMR spectroscopy (uses radio waves to achieve nuclear spin excitation):
Number of different signals = Number of different carbons
o Beware of symmetry!
It will be helpful if you’re comfortable with chemical shifts of
o carbonyl carbons
160-210 ppm
o aromatic carbons
110-150 ppm
Alkene carbons
100-150 ppm
Alkyne carbons
75-100 ppm
C-O carbons
55-90 ppm
C-Cl, C-Br carbons
30-60 ppm
Alkane carbons
0-30 ppm
IR Spectrometry (uses infrared radiation to achieve vibrational excitation):
Be able to recognize the presence of a carbonyl based on an IR spectrum
1700 cm-1
Be able to recognize the presence of a nitrile based on an IR spectrum
2300 cm-1 ALSO ALKYNES
Be able to recognize the presence of a terminal alkyne based on an IR spectrum
3300 cm-1
Be able to recognize the presence of an OH or NH species based on an IR spectrum
3000-3600 cm-1 N-H>O-H>C-H
Understand the relationship between bond strength and the relative energy, or frequency, or
wavelength of radiation will resonate with that bond.
UV/Vis Spectrometry (uses ultra violet and visible radiation to achieve electronic excitation)
Mass Spectrometry (bombards sample with electrons, not light!!):
Be able to recognize the presence of Bromine in a molecule based on mass spectrum
1 to 1 height ratio (around 108 and 110 m/z, 2 m/z apart)
Be able to recognize the presence of Chlorine in a molecule based on mass spectrum
3 to 1 height ratio (around 78 and 80 m/z respectively for one CL, 2 m/z units apart)
Know what the parent peak looks like and what it represents
Know what a radical cation is
Know the type of species a molecule’s fragments must be in order to be detected by Mass spec
Degree of Unsaturation (DoU) is also known as Double Bond Equivalent. If the molecular formula is
given, plug in the numbers into this formula:
DoU=(2C+2+N−X−H)/2