134
CFQ & PP: Solving Combined Spectroscopy Problems
CFQ & PP: Solving Combined Spectroscopy Problems
Reading
Brown and Foote: Section 13.15
Lecture Supplement
Solving Combined Spectroscopy Problems (page 39 of this Thinkbook)
Suggested Text Exercises
Brown and Foote: Chapter 13: 2 – 7, 10 – 13, 18 – 22, 25, 27, 29, 31.
Optional Interactive Organic Chemistry CD and Workbook
Comprehensive Spectroscopy Questions (p. 63)
Concept Focus Questions
There are no Concept Focus Questions specifically for this material.
Refer to the CFQs
for spectroscopy units covered previously in lecture.
Practice Problems
Solving problems is critical to success in mastering organic chemistry. This is especially
true when studying fundamentals of spectroscopy.
There exist a number of excellent
compilations of spectral problems for the undergraduate.
You are encouraged to try some
problems from each site listed below.
WebSpectra (http://www.chem.ucla.edu/~webspectra/): A project of Professor Craig
Merlic at UCLA. Each problem consists of a formula,
1
H-NMR, and
13
C-NMR.
Some
problems have IR, DEPT, or 2D-NMR spectra as well. You will need to measure the
heights of each portion of the integrals of the
1
H-NMR spectrum; no numbers are given.
The structural solution for each problem is given.
Organic Structure Elucidation Workbook (http://www.nd.edu/~smithgrp/structure/
workbook.html): A project of Professor Bradley Smith at the University of Notre Dame.
Each problem consists of a mass spectrum, IR,
1
H-NMR, and
13
C-NMR.
The mass
spectrometry data is not presented in tabular form, so it may be difficult to get accurate
abundance data for the M, M + 1, and M + 2 peaks.
In the real world, or on a Chem 14C
exam, the data will be presented in a tabular form, allowing for precise determination of
the M + 1 and M + 2 abundances. The answers are not given with the problems, so you
can't cheat.
Feel free to bring your answers to Dr. Hardinger to be checked.
On past Hardinger exams, a correct answer for a combined spectral problem was
worth full credit, usually about 35 points.
If the answer was incorrect, analysis of
the spectra may have been worth significant partial credit, so practice showing your
work clearly and in a logical order.