CHEM 293 - Course Outline

The following list contains
- the lecture slides for you to print and annotate, by chapter number as used in the lectures (not the book chapters) and
- the keywords that are covered. Use the keywords as guides when you study for the exams.
Please note that Chapters 3 and 4 below contain separate links to the spectra to print. Do not print the spectra pages too small! I suggest one slide per page.

Disclaimer: For sample spectra taken from the textbook, there may be spectroscopic labels on bands (especially in the IR chapter) that are insufficient for our purposes. This will be addressed in class repeatedly, and you must annotate the slides accordingly. Should you miss class, you must obtain this information from elsewhere! You should then go ahead and make the changes accordingly in the textbook pages. Specifically, for a band just below 3000 cm^-1, the label "C-H" is insufficient, as is the label "C-H stretch". The proper spectroscopic label is "n(C-H)", which is given with the structural information gained, and that is "sp³". This goes for stretching as well as bending vibrations. Check all my solutions carefully against your versions for the proper notation/label!

Chapter 0. Introduction to Spectroscopy

Chapter 1. Molecular Formula and Molar Mass
combustion analysis, percentage composition, empirical formula, molecular formula; index of hydrogen deficiency (unsaturation number); rule of 13; N rule

Chapter 2. UV-Vis Spectroscopy
electromagnetic spectrum; electronic states, molecular orbitals, types of transitions; selection rules; chromophores, hyperchromic, hypochromic, bathochromic, hypsochromic effect; Lambert-Beer law;
materials, instruments; reporting a spectrum; Woodward-Fieser rules for dienes; Woodward rules for enones; aromatic compounds

Chapter 3. IR Spectroscopy
wavenumber, selection rule, types of vibrations: stretching and bending, symmetric and asymmetric, in-plane and out-of-plane;
pseudo-symmetry, overtones, combination bands, Fermi-resonance, total number of vibrational modes, Hooke's law;
instruments, materials;
Spectra (stretching vibrations from 4000 to 1400 cm^-1; substitution patterns for aromatic compounds and for alkenes; CH₂ and CH₃ bending vibrations; overtones; mistakes to avoid)

Chapter 4. NMR Spectroscopy
magnetic moment, precession, Larmor frequency, nuclear spin transitions;
instruments, magnetic field strength; time domain and frequency domain, FID; chemical shift, low/high field, up/down field; materials
¹H spectra: chemical and magnetic equivalence; integration; chemical shift: range and calculation, magnetic anisotropy;
spin-spin coupling, n+1 rule, Pascal's triangle; coupling constant,
Karplus curve; first and second order spectra; coupling for non-equivalence in a group, tree diagrams; protons on oxygen
¹³C spectra: carbon isotopes; chemical shift: range and calculation; spin-spin coupling, proton-coupled, proton-decoupled; integration
2-D spectra: COSY, HETCOR

Chapter 5. Mass Spectrometry
instruments; molecular ion peak, base peak; isotope ratio data for Br and Cl;
general considerations for fragmentations: energy, odd and even electron species, ionization energy, rearrangement;
fragmentations: a-cleavage, benzyl and allyl cleavage, retro-Diels-Alder cleavage, McLafferty rearrangement, onium rearrangement

The spectra in the above links have been taken from one or more of the following sources:
- Pavia, Lampman, Kriz, Vyvyan, Introduction to Spectroscopy, 4^th edition, Brooks/Cole, Belmont, CA, 2009;
- Lambert, Shurvell, Lightner, Cooks, Organic Structural Spectroscopy, Prentice Hall, 1998;
- Silverstein, Webster, Spectrometric Identification of Organic Compounds, 6^th edition, Wiley, 1998;
- Hesse, Meier, Zeeh, Spektroskopische Methoden in der organischen Chemie, 3^rd edition, Thieme, 1987.

Last revised: april17;hmm