COURSES > 2061_11392 - CHEM 0730: UHC ORGANIC CHEMISTRY 1 > COURSE DOCUMENTS > F&W 4 - CHROMATOGRAPHY AND SPECTROSCOPY
F&W 4 - Chromatography and Spectroscopy
Updated: 23 September 2005
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Introduction
This chapter introduces a suite of powerful tools that organic chemists use to determine exactly what the
structure is of a product isolated and purified from their reaction flask. NMR is introduced both in the first
semester Orgo lab and here, in lecture, because of its widespread use in any chemical science today.
Our goal is to be to interpret simple proton NMR spectra of the type assigned in problems and on the old
posted exams. The lecture will be focussed exclusively on the practical aspects of how to use NMR data
to determine structure and that is the only aspect of NMR that I will hold you responsible for. I urge you to
read the entire chapter to get an idea of purification strategies, other proof-of-structure methods, and an
idea of how the NMR experiment works.
Learning Objectives
(1) Be able to use the three pieces of information from proton NMR to determine an appropriate chemical
structure: [a] chemical shift; [b] spin-spin splitting; [c] integration.
(2) Be able to predict (i.e., draw) the proton NMR specturm of many "simple" molecules(i.e., containing
less than 10 carbons and only hydrogens on sp3 hybridized carbons). This includes predicting the
chemical shift, the spin-spin splitting, and the integration for each proton in the target molecule.
(3) Be able to identify the number of unique carbons represented in a 13C-NMR spectrum or to predict the
same given a structure.
(4) Be able to use an IR spectrum to determine if a carbonyl, or an OH/NH functional group.
Lecture Notes
Click here to receive the incomplete lecture notes for NMR, 4 slides per page, in pdf format. (1.336 Mb)
Chemical Shift Table.
Chapter Advice
(1) Focus on how to interpret proton NMR, especially spin-spin coupling, integration, and chemical shift.
(2) Don't worry about numerical calculations involving different frequencies and such, I won't ask you to
describe how the experiment is conducted, but we will rather focus on what the data from the NMR
experiment tells us (the structure!).
(3) Finish this chapter before coming to class on Wednesday, 28 September 2005.
Molecules
Exercises
Do all exercises in the chapter as you read each section.
At the mininium do the following end-of-chapter problems: 3, 4, 5, 6, 8, 13, 14, 15, 16, and 17
For advanced practice, also do these: 7, 10, 11, 12
The UCLA Web Spectra site (http://www.chem.ucla.edu/~webspectra/) is probably the best site to learn
about and practice "proof-of-structure" problems. Lots of good practice problems, broken out by level of
difficulty, etc.
For some "group fun", feel free to solve the spectra problems at this web site:
http://www.chem.uncc.edu/courses/2132/. If you solve these, post a note on the Discussion Board - if you
disagree with a posted answer, post your own answer.
Here's yet another collection of practice problems:
1 of 2
EDIT VIEW
http://orgchem.colorado.edu/hndbksupport/spectprob/problems.html.
2 of 2