Lab Manual

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IMPORTANT NOTICE TO ALL STUDENTS
SAFETY GLASSES OR GOGGLES AND LAB COATS ARE
MANDATORY IN ALL CHEMISTRY LABORATORIES.
STUDENTS CAN PURCHASE THESE SAFETY ITEMS FROM THE
STOREROOM MRN 308.
NO STUDENTS WILL BE ALLOWED TO WORK IN THE
LABORATORY WITHOUT THEIR SAFETY GLASSES.

AVIS IMPORTANT A TOUS LES ETUDIANTS
LES LUNETTES PROTECTRICES ET LES BLOUSES DE
LABORATOIRE SONT OBLIGATOIRES DANS TOUS LES
LABORATOIRES DE CHIMIE.
LES ÉTUDIANTS PEUVENT ACHETER CES ARTICLES
SÉCURITAIRES DANS NOTRE MAGASIN MRN 0308.
AUCUN ÉTUDIANT NE SERA ADMIS DANS LE
LABORATOIRE SANS SES LUNETTES.

1

CHM 1321 Organic
Chemistry
Laboratory
Contents
CHM 1321 Organic Chemistry
1 Thin Layer Chromatography and
Extraction

2 Stereochemistry and Molecular
Models

3 Reduction of 3-Nitroacetophenone

4 Preparation of Benzoic Acid

5 Epoxidation of (R)-(–)-Carvone with
mCPBA

2

6 Nitration of Chlorobenzene

Appendix I – Melting Points

Appendix II – Example of a Good Lab
Report

3

Acknowledgements
Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N 6N5.
January 2012

The Earliest versions of this manual were compiled by Drs. Tony Durst and Denise Chauret. The last few experiments were revised in 2001 by Gordana Babic and Dr. Tito Scaiano. The current version was prepared in 2012 adding four new experiments. Procedures for experiment 1 were graciously provided by Professor Ken Westaway of Laurentian University. Procedures for many of these experiments were tested by Carl Poulin.

Bibliography:
Organic Chemistry Laboratory, 3rd edition, Bell, Clark & Taber, 2001 Laboratory Text for Organic Chemistry, Pasto & Johnson, 1979 Techniques in Organic Chemistry, Mohrig, Hammond, Schatz, Morrill, 2003 Organic Laboratory Techniques, Fessenden, Fessenden & Feist, 2001 Techniques in the Organic Laboratory, Pavia, Pampman, Kriz, Engel, 2002 Experimental Organic Chemistry, 3rd edition, Gilbert & Martin, 2002 Practical Organic Chemistry, 3rd edition, Vogel, 1957

2004-2012 William W. Ogilvie

4

CHM 1321 Introductory Organic
Chemistry
Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N 6N5.
June 2008

NOTICE

Safety glasses or goggles and lab coats are mandatory and must be worn when you are in the laboratory. These items may be purchased at the science stores in the basement or from rd
the chemistry stores in the 3 floor lab.

the equipment. Similarly, while one partner keeps an eye
on the reaction, the other can begin to set up for the next
part of the experiment.
The experiments chosen are reliable and ought to be
completed in the allotted time. If an experiment does not
work as advertised, do not panic. Consult your
demonstrator for advice; in most cases the experiment can
be rescued.

The experiments chosen for this course illustrate
techniques and reactions that are widely used in organic
synthesis, and are designed to acquaint the student with the isolation and purification of organic compounds. Later
experiments have been selected to complement the
accompanying lecture course, and as much as possible have
been scheduled to correspond to the time when the theory
will be discussed in the lecture course. When necessary,
students are expected to read ahead in the text so that
they understand what they will be doing and why.

Safety

READ
THE
BACKGROUND
AND
THE
PROCEDURE FOR EACH EXPERIMENT PRIOR
TO COMING TO THE LABORATORY. THE
DEMONSTRATORS WILL DISMISS ANYONE
WHOSE LACK OF PREPARATION MAY BE
PRESENTING A HAZARD.

Make it a habit to be safety-conscious at all times.
Understand what you are doing and pay attention to details.
If you are uncertain about a procedure ask your
demonstrator.
NO FOOD OR DRINK IN THE LABORATORY

Experiments are done every other week. Experiment
reports must be handed in one week after YOU complete
the experiment at the beginning of the laboratory period.

CELL PHONES AND...
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