Chemistry 350
Organic Chemistry I
Laboratory Manual
,Course team
Author: Dietmar Kennepohl
Laboratory Development
Specialist: Carmen Allen
Laboratory Instructors: Jason Norman, Cherry Ibarra Romero,
Myron Wilde
Course Professor: Dietmar Kennepohl
Every effort has been taken to ensure that these materials comply with
the requirements of copyright clearances and appropriate credits.
Athabasca University will attempt to incorporate in future printings any
corrections which are communicated to it.
The inclusion of any material in this publication is strictly in accord with
the consents obtained and Athabasca University does not authorize or
license any further reproduction or use without the consent of the
copyright holder.
© Athabasca University 2025
Printed in Canada
,CHEM 350 Lab Manual Contents
GENERAL INTRODUCTION 1
ORGANIZATION 2
EVALUATION 2
SAFETY 4
ONLINE LABORATORY RESOURCES 11
EXPERIMENT 1 MELTING-POINT DETERMINATIONS 13
EXPERIMENT 2: RECRYSTALLIZATION 22
EXPERIMENT 3: DISTILLATION 29
EXPERIMENT 4: REFRACTIVE INDEX 36
EXPERIMENT 5: EXTRACTION, SEPARATION AND THE USE OF DRYING AGENTS 42
EXPERIMENT 6: INFRARED SPECTROSCOPY TUTORIAL 62
EXPERIMENT 7: EXTRACTION OF USNIC ACID FROM LICHEN 69
EXPERIMENT 8: PREPARATION OF CYCLOHEXENE FROM CYCLOHEXANOL 79
EXPERIMENT 9: THE NITRATION OF ACETANILIDE 88
LAB DATA SHEET 97
, Acknowledgements
The experiments described in this laboratory manual are mainly
variations of similar experiments that may be found described in the
laboratory manuals of other universities or in commercially produced lab
texts. Each experiment has been modified and rewritten, keeping the
needs of Athabasca University students in mind.
We are indebted to past authors of this lab manual including Lawton
Shaw, David Law, Rob Carmichael, Lois Browne, and Arthur Last. We also
wish to thank Gilda Sanders and Erna Dominey for valuable editing
comments over the years, as well as Aimee Caouette, Blaise MacMullin,
and Ian Grivois, for the artwork and photography. The authors also thank
Lois Browne, Nyron Jaleel, Klaus Thomson, Ross Witherell, Jason Norman,
Cherry Ibarra Romero, Melissa Gajewski for their continuous feedback
and suggestions for improvement to the manual over the years.
Athabasca University also wishes to thank Drs. K. Tanabe and T. Tamura
and for all the infrared spectra used in this manual, obtained from the
SDBS web site: https://sdbs.db.aist.go.jp/sdbs/cgi-
bin/direct_frame_top.cgi
Organic Chemistry I
Laboratory Manual
,Course team
Author: Dietmar Kennepohl
Laboratory Development
Specialist: Carmen Allen
Laboratory Instructors: Jason Norman, Cherry Ibarra Romero,
Myron Wilde
Course Professor: Dietmar Kennepohl
Every effort has been taken to ensure that these materials comply with
the requirements of copyright clearances and appropriate credits.
Athabasca University will attempt to incorporate in future printings any
corrections which are communicated to it.
The inclusion of any material in this publication is strictly in accord with
the consents obtained and Athabasca University does not authorize or
license any further reproduction or use without the consent of the
copyright holder.
© Athabasca University 2025
Printed in Canada
,CHEM 350 Lab Manual Contents
GENERAL INTRODUCTION 1
ORGANIZATION 2
EVALUATION 2
SAFETY 4
ONLINE LABORATORY RESOURCES 11
EXPERIMENT 1 MELTING-POINT DETERMINATIONS 13
EXPERIMENT 2: RECRYSTALLIZATION 22
EXPERIMENT 3: DISTILLATION 29
EXPERIMENT 4: REFRACTIVE INDEX 36
EXPERIMENT 5: EXTRACTION, SEPARATION AND THE USE OF DRYING AGENTS 42
EXPERIMENT 6: INFRARED SPECTROSCOPY TUTORIAL 62
EXPERIMENT 7: EXTRACTION OF USNIC ACID FROM LICHEN 69
EXPERIMENT 8: PREPARATION OF CYCLOHEXENE FROM CYCLOHEXANOL 79
EXPERIMENT 9: THE NITRATION OF ACETANILIDE 88
LAB DATA SHEET 97
, Acknowledgements
The experiments described in this laboratory manual are mainly
variations of similar experiments that may be found described in the
laboratory manuals of other universities or in commercially produced lab
texts. Each experiment has been modified and rewritten, keeping the
needs of Athabasca University students in mind.
We are indebted to past authors of this lab manual including Lawton
Shaw, David Law, Rob Carmichael, Lois Browne, and Arthur Last. We also
wish to thank Gilda Sanders and Erna Dominey for valuable editing
comments over the years, as well as Aimee Caouette, Blaise MacMullin,
and Ian Grivois, for the artwork and photography. The authors also thank
Lois Browne, Nyron Jaleel, Klaus Thomson, Ross Witherell, Jason Norman,
Cherry Ibarra Romero, Melissa Gajewski for their continuous feedback
and suggestions for improvement to the manual over the years.
Athabasca University also wishes to thank Drs. K. Tanabe and T. Tamura
and for all the infrared spectra used in this manual, obtained from the
SDBS web site: https://sdbs.db.aist.go.jp/sdbs/cgi-
bin/direct_frame_top.cgi
