Chem 2253 Final Exam Study Guide

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

Be able to determine degrees of unsaturation from a chemical formula

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

 is the number of carbons

 N
 is the number of nitrogens
 X
 is the number of halogens (F, Cl, Br, I)
 H is the number of hydrogens

Know what two things can cause a degree of unsaturation

Rings and Pi bonds
Be able to provide the structure of molecules based on nothing but spectral data.