TENNESSEE STATE UNIVERSITY

DEPARTMENT OF CHEMISTRY
CHEM 2011-00: Organic Chemistry I Laboratory
Spring 2016
Instructors Name: Dr. Al-Masum
Office Location:
Boswell 220/208G
Phone:
(615)-963-5339
E-mail:
malmasum@tnstate,.edu
Class Hours
TWR 10:10-1:10 PM Boswell 227
Office Hours: 1:00-2:00 Monday

Textbook:

Macroscale and Microscale Organic Experiments, 5th edition, Kenneth L.

Williamson; Brooks Cole, 2006 [ISBN-13: 978-0618590674]

Prerequisite: Second Term General Chemistry Lecture and Lab

Objective:
This course is designed or chemistry majors, pre-professionals, biology and other
scientific areas. Its aims are to expose students to some of the important experimental techniques,
equipment and reactions in organic chemistry, and to illustrate the chemical reactions and
properties of molecules discussed in lecture.
Course Description: This course exposes students to some of the important experimental
techniques, equipment and reactions in organic chemistry. In addition, the course illustrates the
chemical reactions and properties of molecules discussed in lecture. Students will have hands-on
experiences with purification methods such as: crystallization, distillation, extraction, TLC,
column chromatography etc. The course also involves organic synthesis, purification and
identification using melting points and spectroscopic techniques.
Course Competencies: Upon completion of this course, the student should have obtained the
following competencies:

A thorough understanding of the common isolation and purification techniques used in

organic chemistry
A working knowledge of the important spectroscopic techniques used for characterization
and identification of organic molecules
A working knowledge of the equipment and techniques used in performing simple
organic synthesis
Analyze mixture of compounds by TLC
Set up and perform simple and fractional distillation and learn the efficiency of both
techniques
A thorough understanding of the scientific writing process

GRADING:

Notebook grade
Formal report (1)
Workstation Organization/Tidiness and Teamwork
Final Exam

= 50% of total grade

= 20% of total grade
= 10% of total grade
= 20% of total grade

LABORATORY REPORTS AND DUE DATES:

LATE LABORATORY REPORT: Any laboratory report not turned in on or before the due
date will be assessed a 10-point penalty per day. Reports will not be accepted if they are past due
more than two days.
OUTLINES: A detail outline of the experimental procedure for each experiment must be
completed before coming to class. The outline will help you complete the lab faster and also
help you better understand the experiment.
ATTENDANCE AND EXPECTATIONS: Students are expected to regularly attend all classes
in this course for credit and to complete all required work in this course. There are no makeups for any laboratory experiments. Students are expected to read the Undergraduate Catalog
for further instructions on attendance policy. Students who miss more than one (1) laboratory
periods should consider re-taking this course.
SAFETY GOGGLES: Safety Goggles are required in this course. No student will be
allowed to work in the laboratory without a pair of Safety Goggles. Safety Goggles must
be worn at all times while in the laboratory.
TSU Statement of Disability Policy for Students
It is the policy of TSU to accommodate students with disabilities, pursuant to federal law, state
law, and the Universitys commitment to equal educational opportunities. Any student with a
disability who needs accommodations, for example in seating placement or in arrangements for
examinations, should inform the instructor at the beginning of the course. Students with
disabilities are encouraged to contact the Office of Disabled Student Services, which is located in
Kean Hall, Room 117, Telephone 963-7400 or 963-7872.

EXPERIMENTS:
Day

Reading Assignments

Check-In Procedures. Chapter 1: Introduction, Laboratory notebook writing and related

calculation. Chapter 2: Laboratory Safety and waste disposal. Safety Quiz

Chapter 3: Melting Points and

Boiling Points (pp 38-58)

Chapter 4: Recrystallization (pp 6187)

Experiments

Expt. 1: Calibration of Thermometer (p 51)

Expt 2: Microscale procedure for pure Urea and
Cinnamic Acid (p-52)
Expt 3: Melting Points of Urea-Cinnamic Acid Mixtures
(p 53)
Expt. 4: Melting Points of Unknowns (p 53)

Expt.1. Solubility Tests (p 79)

Expt. 2: Microscale procedure for Phthalic Acid (p 81)

Expt 2A: Fractional Distillation of Cyclohexane

andToluene Mixture (p-98)
Expt. 6: Fractional Distillation of Unknowns (103)

Chapter 5: Distillation (pp 88-104)

Chapter 5: Continue

Expt 1: Separation of a Carboxylic Acid, a phenol, and

a Neutral Substance (p-151)

Chapter 7: Extraction (pp 135-171)

Expt 6: Extraction of Caffeine from Tea (p-162-164)

Hand out Aldehyde Functional

Groups

Tollens Test Silver mirror experiment

Chapter 8: Thin Layer

Chromatography: Analysis of
Analgesics and Isolation of
Lycopene from Tomato Paste (pp
172-193)

Expt 1: Analgesics (p-183)

Chapter 9: Column Chromatography

Expt 4: Chromatography of the Ferrocene and

Acetylferrocene (p 210-211)

10

Chapter 16: The SN2 Reaction- 1Bromobutane (pp 325-332)

Expt 1: Synthesis of 1-Bromobutane (p 327)

11

Chapter 19: Alkenes from Alcohol.

Cyclohexene from Cyclohexanol
(pp 351-356)

Expt: 1: The Preparation of Cyclohexene (p 352)

12

Review session and Check-Out

Final Exam. Lab reports and Lab notebooks will be collected for grading.
13

GENERAL LAB DIRECTIONS

A.
1.
2.
3.
4.
5.
6.
7.

B.
1.
2.

Planning and Efficiency

Plan your lab work ahead of time. This is essential if you expect to complete an experiment within the
allotted time. Furthermore, you will have some understanding of what you are doing.
Read the experiment and all reference material before coming to lab. (Prepare a complete outline of the
experiment).
Make good use of your time. When you are waiting for something to dry, or waiting for something to cool, etc.,
start on or prepare for the next step or experiment. Learn to do more than one thing at a time.
Listen for announcements from your T.A. and/or instructor. Periodically check the lab blackboard for notices.
Do not be afraid to ask the instructor questions about the experiment. They (we) are here to help you. At the
same time, you should be prepared for them to ask you questions about the experiment or technique.
Every student in this course is required to do his or her own work: this includes all experimental work,
calculations, and reports.
Be sure to label all solutions or chemicals in your desk so you do not mix them up. Do not rely on your
memory. Use pencil to label. Do not use tape or ink.
Upon entering the lab, you will be assigned to a specific locker and work area. Its a good idea to keep a towel
in your locker. It is your responsibility to keep your work area, adjacent sink, and floor clean. Failure to do so
will affect your grade. You are responsible for, together with your fellow students, for the cleanliness of
community equipment - balances, hoods, and reagent tables. Again failure to assist in keeping the laboratory
clean will lower your grade.
General Comments Regarding Notebook
Your notebook is the only record you have of your work in the lab.
You must use a bound composition notebook. Loose pages, three-ring notebooks, or spiral notebooks are
not accepted.

3.
4.
5.
6.

The pages in the notebook should be numbered. The first 6 pages should be an up-to-date Table of
Contents so that any experiment can be located quickly.
All entries in the notebook must be in ink. A mistake is not erased, but crossed out with a single line and
replaced with the correction written above.
All data obtained in the laboratory are recorded in the notebook at the time the data are obtained.
Recording data on loose scraps of paper is not acceptable.
Your notebook must be sufficiently neat that someone else (especially the instructor) can read and
understand it. Use plenty of space. Remember, you will have to extract data from your notebook to
calculate results and more importantly write reports.

C.
Format of Notebook:
Must write your Name, Course Name, and Instructors Name on front page of the notebook
1.
Reserve pages 1-4 for Table of Contents. Keep Table of Contents current.
2.
Start Experiment 1 at the top of page 5.
3.
For each new experiment, begin at the top of a new right-hand page.
4.
For each experiment, begin with the following items:
I.
Title of the experiment, date of experiment
Equation of the Experiment
Table of reagents
II.
A brief (3-4 sentences) statement of introduction, purpose, and principles on which the
experiment(s) is based. Relevant balanced chemical equations should appear here when
applicable.
III.
An outline of the procedure to be followed.
IV
During experiment: A complete and neat lists of data taken during the experiment. Data must be
properly identified and labeled and presented in a logical order. Use appropriate structural
drawings when necessary. Use tables where appropriate.
V.
All other observations that you make during the course of the experiment should also be recorded.
Examples include: color changes, changes you make in the general procedure, observed errors
such as adding to much solvent or solute or too much of a certain reagent. If you are in doubt as to
if the observation is relevant, make a note of it in your notebook. Do not trust your memory!

***** Sections I, II and III above must be completed before coming to the lab. This work will
credit you 10 % of Notebook grade. This will save significant time during the lab period.
*******
The Chemistry Laboratory Formal Report
There is not one absolutely correct format or method for writing up a laboratory report. The format given below is
for a published experimental study and is the format that is expected in general. The goal is to "include everything
necessary in the shortest possible way." Standard English is required, and everything that is written must be
scientifically sound and logical.
I.

Title Page:
This should as specific as possible. State the actual substances used and the method: Determination of the
Molar Mass of Acetone by the Dumas Method.
1. Name:
2. Date Experiment Started and Date Finished
3. Date Submitted
II.

Abstract
Put on the next page. In general, summarize the results of the experiment and state any significant conclusions.
Specifically:
1. State the method used, and actual experimental values that you obtained with uncertainties
2. If there are literature values, put these here as well; (this is not necessary when actually publishing, but it
is good practice for in-house reports, unless there are many literature values).

3.

Put statement comparing your results with the literature values. If there is disagreement exceeding
experimental error, state a plausible reason why there is a difference.

III. Introduction
1. State the purpose of the experiment.
2. Give a brief outline of the theory behind the experiment as well as any pertinent definitions. This includes
the "working equation(s)" that will be used in treating your experimental data and the actual experiment
quantities to be measured.
3. Make sure that all symbols are defined in any equations that are used.
IV. Experimental Method
1. Cite the lab manual where the original procedure was obtained. This would be a good "first sentence" for
this section. Here is a sample sentence along with two ways of citing a reference:
a).
The method as given by Crockford et al. Was followed, except that heating mantle was used in
place of a micro-burner (1).
b)
The method as given by Crockford et al. Was followed, except that heating mantle was used in
place of a micro-burner.1
2. As shown above any modifications to the procedure in the reference should be noted.
3. Give a brief description of the procedure
4. This section is always written in the past tense (was, were, was used, etc.)
5. State the number of runs made and the conditions (concentrations, temperatures, etc.) at the end of this
section.
V. Results
1. Tabulate the data that were measured. Tables should have a title with units, and explanatory captions. Do
not exclude data if it seems out of line. The cause of this discordant data should be pointed out in the
Discussion. Your final calculated results with error estimates should be listed in this section. Sometimes,
data can be presented in form of graphs, in which case it is not necessary to tabulate it. A common
example would be in a freezing point determination, a plot of time versus temperature would suffice for
this data. Then report the actual freezing point from the graph in the results section.
2. Give a typical calculation (avoid the details). If the calculation is excessively long, it may be placed in the
end in an Appendix.
3. Any graphs of data should be included in this section. Here are rules for graphs, especially if they are hand
drawn.
A). Title the graph
B). Label the X and Y axis with units
C). Use "x's" to make the data points, not individual dots. Dots with circles, triangles, squares,
etc. are fine.
D). Label any lines drawn in
E). The data points should cover at least half of the paper, especially for hand-drawn graphs.
VI.
1.
2.
3.
4.
5.
6.
7.
VII.

Discussion
This is the most flexible section. It should always include:
A comparison of your results with literature values
Plausible reasons for discrepancies with the accepted values
Possible systematic errors and ways to reduce them
Improvements for the experimental technique
Special circumstances or difficulties that may have influenced the results
Suggestions of experiments to confirm suspicions of discrepancies of your results with accepted values
Suggestions of new/different chemical systems which may be interesting to try in the future
References
1.
The book title can be either in italics or in quotations.
Garland, D. P.; Garland, C. W.; Nibler, J. W. Experiments in Physical Chemistry, 6th ed. McGrawHill: New York, 1996.
2.
A book with a plethora of information and an editor (like CRC Handbook of Chemistry and
Physics):

3.

4.

5.

Handbook of Chemistry and Physics, 72nd edition., R. C. Weast, editor, p F-10, CRC Press, Boca
Raton, Florida, 1991
A book with many authors (say 10 or more) with some editors:
Justice, J. C. In Comprehensive Treatise of Electrochemistry, Vol. 5, Thermodynamic and
Transport Properties of Aqueous and Molten Electrolytes; Conway, B.E.; Bokris, J. O'M; Yeager,
E. Eds.; Plenum: New York, 1983; pp. 223-337.
A journal Article:
Gunning, H. E.; Gordon, A. R. J. Chem. Phys. 1942, 10, 126.
Here the year is in bold, the volume italicized, and the last number is the first page number. An
option here is to underline the volume, and use regular type for both the year and the page number.
A journal Article with Title of the paper:
"Novel methods for the synthesis of functionalized indoles from arylhydroxylamines and activated
acetylenes." Hwu, J.R.; Patel, H.V.; Lin, R.J.; Gray, M.O. J. Org. Chem. 1994, 59, 1577-1582 and
references cited therein.
Session I -- Five Week Session
May 31 Classes begin
June 1-2 Late registration/Drop/Add
June 16 Last day to withdraw from First-session courses
June 16 Last day to withdraw from University
July 1 Last day of classes
July 4 Holiday Observed
July 6 Faculty must have posted all grades via MyTSU