Journal of Chemical Education is archived here with a number of good project possibilities Chemistry 320
Organic Laboratory Methods
Spring Semester, 2020
Lecture: Wednesday 2:00-3:15
Laboratory: Monday and Thursday, 2:00-4:50
Instructor:
William A. Price, Ph.D.
Holroyd 345
(215)-951-1261
price@lasalle.edu
Text:
No required text. We will occasionally use material from R.M. Silverstein, F.X. Webster, D.J. Kiemle, Spectrometric Identification
of Organic Compounds, 8th Edition, John W. Wiley & Sons, New York, 2014 (7th edition is fine). If you can get an older edition, it would be useful.
Required Materials:
Composition Notebook
Laboratory goggles and apron or lab coat
3-ring binder
Course Description and Learning Objectives:
After completing this course students will
• be proficient in writing papers (reports) coherently and concisely using a scientific style (ACS guidelines);
• cite references using proper ACS citation format;
• use drawing programs to illustrate reactions and mechanisms
• be proficient in organizing and delivering a seminar;
• be able to read and interpret articles in the literature;
• be able to carry out experiments using literature procedures;
• be able to carry out literature searches using advanced scientific data bases;
• gain independence in the laboratory;
• understand the many nuances of organic synthesis including the practical applications of green chemistry and asymmetric synthesis
• learn to use and interpret data derived from IR and GC/MS instruments;
• be able to operate and interpret complex spectra derived from the 400 MHz NMR spectrometer.
LECTURE:
The lecture portion of the course (Wednesdays 2:00-3:15) will be devoted to several
aspects of spectroscopy as applied to structure elucidation. Particular attention
will be paid to nuclear magnetic resonance (NMR) spectroscopy. Part of every
lecture will also involve a discussion of upcoming and ongoing laboratory
projects. The course will begin with an overview of the NMR phenomenon followed
by coverage of advanced aspects of proton NMR, carbon-13 NMR, correlated spectroscopies.
We will also spend some time discussing mass spectrometry and infrared (IR)
spectroscopy. Learning spectroscopy is akin to learning a foreign language: the more you work at it, you will begin to recognize patterns and your level of comfort will increase.
Numerous slides will need to be downloaded and printed. Some handouts will be distributed throughout the semester, so it is imperative that you maintain an organized binder - particularly since you will be able to use it on some in-class exercises. Problem sets will be assigned dealing with structure elucidation based on chemical and spectral information. The clear benefits of translating spectra into organic structures will allow for a more thorough appreciation and understanding of the physical and structural dynamics of organic chemistry.
Occasionally, we will have a problem of the week that you should work through before the next lecture. Links to each problem are below.
NMR ppt review / Proton NMR review problem set
Literature Search: Problem Set 1 due 1/30/20
Problem #1 for 1/29/20 /// Problem #2 for 2/12/20 /// Problem #3 for 2/26/20
C-13 NMR ppt slides Proton NMR ppt slides
Proton NMR III coupling to F-19, P-31, D2O exchange, homonuclear decoupling
NMR III DEPT, COSY, and HETCOR spectra
hypothetical spin systems - 2 problems
Mass Spectrometry I ppt slides Mass Spec. Problem Set
LABORATORY:
It has long been suggested that most of one’s learning in the field of
chemistry takes place in the laboratory. This course clearly subscribes to that
premise. The laboratory portion of CHM 320 consists of six
short (2-3 week) projects designed to introduce a variety of new synthetic
techniques, reaction types, separation methods, instrumental methods and overall,
an enhanced diagnostic thought process. The goal is to develop the tools to solve scientific questions through experimentation and creative problem solving.
Some of the projects will be carried out in pairs. It is essential that the
project background reading be completed prior to a lab day since occasionally
some preliminary laboratory work is necessary (finding glassware and equipment, drying reagents, glassware,
etc.). Realistically, synthetic chemistry does not fit nicely into 3 hour blocks
of time and so you should expect to spend some lab/instrumentation time outside
of class. Each student is required to maintain a complete notebook throughout the semester. A careful record of all experimental conditions, observations, and data (including physical properties and spectral parameters) should be kept. These will be checked periodically PROJECT DETAILS
(pdf)
Journal of Chemical Education is archived here with a number of good project possibilities
MolView - versatile 3-D molecule drawing and visualization site
Percent Yield and Atom Economy calculations some slides
Atom Economy decscribed with examples
Sharpless Asymmetric Dihydroxylation ppt slides
olefin metathesis (ppt)
Cover sheet for independent project proposal details; include this sheet with your proposal
Demystifying Synthetic Organic Laboratory Technique helpful tidbits of wisdom on all aspects of synthesis
SEARCHING ON THE WEB:
SciFinder Scholar Web Edition Register and log on using your lasalle.edu email address
A significant portion of research will require that you use SciFinder Scholar. Five of the laboratory
projects are accompanied by lead references to journal articles that
give experimental details. There are also references that are cited within those articles that will be helpful as well. You should keep all of the papers in your binder. You should locate these articles very
early in the course since some may have to retrieved through inter-library loan
services.
ChemSpider is an interactive
database of synthetic procedures. Register (it's free) and have access to innumerable
procedures that you may find helpful as you search for a project. ACS Web Editions
is now available through the library for immediate access to over 30 ACS journals (including J. Chem. Ed.)One problem set will focus on literature searching using on-line searching
techniques.
La Salle subscribes to SciFinder Scholar which each of you will need to register for. Other helpful databases can be found in First-Search
and Proquest. Some advanced texts, spectral indices and reference books will
also be needed.
Laboratory Reports:
All laboratory reports will be written as if being submitted for publication.
The format and style that will be followed can be found in Guidelines
for Writing Laboratory Reports at La Salle University. Each report will
include the following: title, author(s), date submitted, an abstract, introduction with structures and reactions, any pertinent theory (mechanism, e.g.) and background
information, results and discussion (including spectral interpretation), conclusion,
experimental section, and literature cited. All relevant spectra should be appended,
but only those that are referred to in the text of your paper. All tables and
figures should be imbedded in the text of the report, must have titles and must
be referred to in the text of the paper. Structures should be drawn with a drawing
program (e.g. KnowItAll, chemwindows, etc.).
Each write-up will begin with a 2-3 sentence abstract that generally discusses
the scope of the project. Articles published in J. Org. Chem. or Synthesis
will provide numerous examples of appropriate abstracts and experimental sections.
The special project will be presented as a seminar with slides (lasting 12-15 minutes). The reports are due on the dates listed. Timely submissions (instructor’s judgement)
can be resubmitted after initial grading for a re-grade. A 5% penalty will be assessed to papers
for each day the paper is late according to the schedule below.
1st report due February 5
2nd report due February 26
3rd report due March 25
4th report due April 8
5th report due April 22
Seminar (6th report) is on April 30 at 2PM
Grading:
A breakdown for the grading in this course will be as follows (the instructor
reserves the right to modify this as necessary):
5 laboratory reports 500 pts
1 seminar presentation 100 pts
problem sets 150 pts
mid-term exam 125 pts
final exam 125 pts
Total 1000 pts