Course Syllabus

Course Information

CHM2023 Intro to Org. Chemistry I Lab Recitation W 9:30-10:20am FN2.104

CHM2123 Intro to Organic Chemistry Laboratory I MW 1:00-4:45pm BE2.330
Note: You may not take lab without recitation, no exceptions will be made.

Professor Contact Information

Dr. Donovan C. Haines

Phone: 972-883-4542
Email: haines@utdallas.edu
Office: BE2.518

Office Hours: MW 11am-noon (I may be occasionally in the lab during long

experiments)

Course Pre-requisites, Co-requisites, and/or Other Restrictions

Prerequisite: CHEM 2323 (may be taken concurrently), and one year of General
Chemistry theory and experiments (as required by 2323).

You must be able to attend the entire laboratory and recitation sessions to take this
course.

Course Syllabus Page 1

Course Description

This course is an introduction to basic experimental technique and chemical information

sources. Major topics include safety, record keeping, written communication, information
sources, physical separations, determination of physical constants, purification and
characterization techniques, and basic organic reactions. An important goal of this course
is to master technique before shifting the focus to outcome in Organic Chem. Lab II.
Correlation with the organic lecture occurs where possible, but practical factors prevent
full overlap.

Student Learning Objectives/Outcomes

Course Objectives: This course provides an introduction to basic experimental technique and
chemical information sources. Students who successfully complete this course acquire skills that
incorporate safety and record keeping protocols, verbal and written communication, use of
information sources, and knowledge of simple organic reactions and the separation,
characterization, and purification techniques associated with them.

Expected Learning Outcomes: Upon completion of this course, students will

1. Be able to describe and utilize safety protocols associated with basic organic chemistry
laboratory operations.
2. Know how to keep written records, produce reports of experiments, interpret experimental
data and draw relevant conclusions.
3. Be able to prepare, purify, and characterize simple organic compounds.
4. Know how to work and communicate effectively in small groups and teams.

Course Syllabus Page 2

Required Textbooks and Materials

TEXTBOOK: Pavia, Lampman, Kriz, and Engel. Organic Laboratory Techniques: A

Microscale Approach. 3rd ed. Fort Worth: Saunders, 1999.

SUPPLIES: The list below is good for two semesters of organic lab. Supplies must be
obtained by the second week.
HARDBOUND NOTEBOOK with duplicate sheets (carbon copies)
APPROVED SAFETY GLASSES: Must have the Z87 code engraved on them.
The spectacle type is sufficient for most people. They look like regular glasses
and can be worn over prescription glasses. Goggles provide much better
protection but may cause discomfort due to the rubber band that wraps around the
user’s head and may cause certain individuals to sweat copiously.
DISHWASHING GLOVES: Can be obtained at any store.

Suggested Course Materials

SUPPLIES: The list below is good for two semesters of organic lab.
PROTECTIVE CLOTHING: A lab coat is strongly recommended. Coats can be
obtained at retail outlets such as Sears, and at most uniform and medical supplies
stores.
ITEMS OF PERSONAL USE: Hand soap, towel, economy sponge pack,
tweezers, marker or pen, and masking tape (used for labeling).

Course Syllabus Page 3

Assignments & Academic Calendar

Recitation and Lab Schedule (Numbers represent experiment numbers in the course
textbook):
Day Date Recitation Lab
W 5/31/2006 Introduction
M 6/5/2006 Checkin/Safety
W 6/7/2006 7/3 7
M 6/12/2006 3
W 6/14/2006 4/5 4
M 6/19/2006 5
W 6/21/2006 15/12 15
M 6/26/2006 12
W 6/28/2006 21/23 21
M 7/3/2006 23
(No lab - IR
W 7/5/2006 47 exercise)
M 7/10/2006 47
FINAL Checkout/course
W 7/12/2006 EXAM review
M 7/17/2006
W 7/19/2006

REPORTS.
This term may refer to either assignments or experiment records. Assignments are
typically completed outside the lab and handed in using a specified format.
Experiment records result from work performed in the organic lab and must
always be written in the lab notebook. All reports are graded on a 100 point scale.
For a set of guidelines on how to write lab reports refer to the Guide for writing
lab reports, available at the instructor’s website under CLASS MATERIALS.
Experiment reports are due at the beginning of lab one week after the lab is
completed (if experiment 7 is completed on Wed. 6/7, it will be due Wed. 6/14 on
your way into lab).

The description of how to write reports on experiments, how points are assigned
to the various sections, and examples are given as a supplement to this syllabus
that was written by Dr. Cortes.

QUIZZES
There will be weekly quizzes in WebCT (see WebCT information later in this
syllabus) that start on Wednesday and must be completed by 11pm the the
following Tuesday. Quizzes cover the subjects covered in recitation and safety
information presented in the first laboratory session (For example, the quiz that
can be accessed starting 5/31 will cover the course introduction and safety; that
accessible on 6/7 will cover experiments 7 and 3). Quizzes will cover both the

Course Syllabus Page 4

 practice of and theory behind the experiments, including safety issues. Students
may not work together on quizzes. To enforce recitation attendance, specific
information required to answer some quiz questions may be presented in
recitation (For example, “the answer to quiz question three will be ‘mass action’”.
These questions may have nothing to do with the experiments for that week (the
only way to know the answer is to attend recitation).

FINAL EXAM
The final exam will be taken during recitation time in the normal recitation room.
It will be a comprehensive exam covering both the theory and practice of all
experiments the course covers during the semester, as well as any safety
information presented during the course of the semester.
To prevent cheating, no student arriving late will be allowed to take the exam
after the first student has finshed.

READING AND PROBLEM ASSIGNMENTS

You should read the reading assignments prior to coming to the recitation
covering the indicated experiments.

Exp. 7. ANALGESIC DRUGS AND ISOLATION OF ACTIVE INGREDIENT.

Solid-liquid extraction, filtration, and melting point determination.
• Readings: p. 96-99, 105-109, and “required readings” indicated on p. 97.
• Assigned questions from exp. 7: # 1-5. Please include with your lab
report.
Exp. 3 a & b. CRYSTALLIZATION. Basic technique and uses, vacuum filtration.
• Readings: p. 60-67, questions on p. 70, and readings indicated on p. 63.
• Assigned questions from the textbook: # 1. Please include with your lab
report.
Exp. 4 a & b. EXTRACTION. Liquid-liquid extraction, miscibility & solubility
issues, distribution coefficient.
• Readings: p. 71-79, 595-605, 607-611, and 119-123.
• Assigned questions from the textbook: # 1. Please include with your lab
report.
Exp. 5 a & b. THIN LAYER CHROMATOGRAPHY (TLC). Basic theory and
practice of chromatographic separations.
• Readings: p. 80-83, 697-699, and 702-710.
• Assigned questions from the textbook: # 3. Please include with your lab
report.
Exp. 15 a – c. ISOLATION OF PIGMENTS FROM SPINACH. Combined use of
column chromatography and TLC to isolate and identify natural products.
• Readings: p. 158-164, 669-680, and 684-688.
• Assigned questions from the textbook: # 1. 3, 4. Please include with your
lab report.
Exp. 12. CHEMICAL SYNTHESIS: PREPARATION OF ISOPENTYL
ACETATE.

Course Syllabus Page 5

 Esterification, reflux, simple distillation, boiling point determination,
driving equilibrium reactions.
• Readings: p. 128-133, 135, 585-586, 589-590, 617-627.
• Assigned questions from the textbook: 3-7 and 9. Please include with
your lab report.
INFRARED SPECTROSCOPY. Introduction to organic spectroscopy and
structure determination.
• Readings: Appendix 3, p. A14-A32.
• Assignment: IR interpretation exercise. Obtain this exercise from the
instructor’s website.
Counts as a report (100 pts), and it’s due on the next lab period.
Exp. 21 a & c. SYNTHESIS OF ALKYL HALIDES AND NUCLEOPHILIC
SUBSTITUTIONS.
Illustration of Sn1 and Sn2 reactions applied to the synthesis of alkyl
halides.
• Readings: p. 208-211, 213-215.
• Assigned questions from the textbook: For n-Butyl bromide: 1 and 3-5.
For t-Butyl chloride: 3, 5, 8.
Exp. 23 a. ELIMINATION REACTIONS: DEHYDRATION OF 4-
METHYLCYCLOHEXANOL.
Illustration of acid-catalyzed E1 reaction, alkene synthesis, tests for
unsaturation, IR analysis.
• Readings: p. 222-225, 226-227.
• Assigned questions from the textbook: 1, 2(a-d), and 3. Please include
with your lab report.
Exp. 47 b. PREPARATION OF NYLON. Polymerizations and types of polymers.
• Readings: p. 385-398.
• Assigned questions: # 2, 5.

Course Syllabus Page 6

Grading Policy

Your grade will be compiled as follows…

Numerical average
Quizzes (the lowest one will be dropped) 20%
Reports (the lowest two will be dropped) 60%
Final Exam 20%

Letter grade
A+ 95.000 - 100.000
A 90.000 - 94.999
A- 85.000 - 89.999
B+ 80.000 - 84.999
B 75.000 - 79.999
B- 70.000 - 74.999
C+ 65.000 - 69.000
C 60.000 - 64.999
C- 55.000 - 59.999
D+ 50.000 - 54.000
D 45.000 - 49.999
D- 40.000 - 44.999
F Below 40.000

IMPORTANT NOTICE: You MUST complete at least 75% of the experiments in this
class to receive a passing grade. Any student missing more than 25% of the scheduled
experiments should drop the course or will receive a failing grade.

Because many of our experiments require the preparation of fresh reagents with a limited
useful life, and the number of chemicals placed out during lab must be limited for saftety
reasons, there is no ability to makeup missed experiments.

Reports turned in late will carry a 10% per day deduction for lateness, with a maximum
penalty of 50%. Reports may not be turned in for credit after the Final Exam.

Course & Instructor Policies

UNSAFE BEHAVIOR including horseplay and pranks in the chemistry lab can be
dangerous and precipitate accidents. Therefore, the lab coordinator and the lab staff
reserve the right to reprimand, penalize, or even dismiss students who consistently
disregard the rules of etiquette.

PUNCTUALITY POLICY. Students who are late invariably cause unnecessary delays
and strain in the organic lab schedule. After the first 15 minutes, any students who arrive

Course Syllabus Page 7

late to the lab session without a justifiable reason will receive a 20 point deduction from
the corresponding lab report.

TIDINESS. It is imperative that you clean after yourself after every experiment, or others
will have to do it. As a matter of courtesy to others, always leave the work space as you
would like to find it. Students who repeatedly do not clean up properly will face point
deductions (20%) on the appropriate experimental reports.

CHECKING EQUIPMENT IN AND OUT. You will receive a drawer with equipment
that you will be responsible for during the semester. Any equipment missing from your
drawer at checkout time will be charged to your student account. If you quit attending or
drop the course, you must check out as soon as possible to avoid unnecessary charges to
your account.

Field Trip Policies

Off-campus Instruction and Course Activities

Off-campus, out-of-state, and foreign instruction and activities are subject to state
law and University policies and procedures regarding travel and risk-related
activities. Information regarding these rules and regulations may be found at the
website address
http://www.utdallas.edu/BusinessAffairs/Travel_Risk_Activities.htm. Additional
information is available from the office of the school dean. Below is a description
of any travel and/or risk-related activity associated with this course.

There is no travel associated with this laboratory course.

Student Conduct & Discipline

The University of Texas System and The University of Texas at Dallas have rules
and regulations for the orderly and efficient conduct of their business. It is the
responsibility of each student and each student organization to be knowledgeable
about the rules and regulations which govern student conduct and activities.
General information on student conduct and discipline is contained in the UTD
publication, A to Z Guide, which is provided to all registered students each
academic year.

The University of Texas at Dallas administers student discipline within the

procedures of recognized and established due process. Procedures are defined
and described in the Rules and Regulations, Board of Regents, The University of
Texas System, Part 1, Chapter VI, Section 3, and in Title V, Rules on Student
Services and Activities of the university’s Handbook of Operating Procedures.
Copies of these rules and regulations are available to students in the Office of the

Course Syllabus Page 8

 Dean of Students, where staff members are available to assist students in
interpreting the rules and regulations (SU 1.602, 972/883-6391).

A student at the university neither loses the rights nor escapes the responsibilities
of citizenship. He or she is expected to obey federal, state, and local laws as well
as the Regents’ Rules, university regulations, and administrative rules. Students
are subject to discipline for violating the standards of conduct whether such
conduct takes place on or off campus, or whether civil or criminal penalties are
also imposed for such conduct.

Academic Integrity

The faculty expects from its students a high level of responsibility and academic
honesty. Because the value of an academic degree depends upon the absolute
integrity of the work done by the student for that degree, it is imperative that a
student demonstrate a high standard of individual honor in his or her scholastic
work.

Scholastic dishonesty includes, but is not limited to, statements, acts or omissions
related to applications for enrollment or the award of a degree, and/or the
submission as one’s own work or material that is not one’s own. As a general
rule, scholastic dishonesty involves one of the following acts: cheating,
plagiarism, collusion and/or falsifying academic records. Students suspected of
academic dishonesty are subject to disciplinary proceedings.

Plagiarism, especially from the web, from portions of papers for other classes, and
from any other source is unacceptable and will be dealt with under the
university’s policy on plagiarism (see general catalog for details). This course
will use the resources of turnitin.com, which searches the web for possible
plagiarism and is over 90% effective.

Email Use

The University of Texas at Dallas recognizes the value and efficiency of

communication between faculty/staff and students through electronic mail. At the
same time, email raises some issues concerning security and the identity of each
individual in an email exchange. The university encourages all official student
email correspondence be sent only to a student’s U.T. Dallas email address and
that faculty and staff consider email from students official only if it originates
from a UTD student account. This allows the university to maintain a high degree
of confidence in the identity of all individual corresponding and the security of
the transmitted information. UTD furnishes each student with a free email
account that is to be used in all communication with university personnel. The
Department of Information Resources at U.T. Dallas provides a method for
students to have their U.T. Dallas mail forwarded to other accounts.

Course Syllabus Page 9

Withdrawal from Class

The administration of this institution has set deadlines for withdrawal of any
college-level courses. These dates and times are published in that semester's
course catalog. Administration procedures must be followed. It is the student's
responsibility to handle withdrawal requirements from any class. In other words, I
cannot drop or withdraw any student. You must do the proper paperwork to
ensure that you will not receive a final grade of "F" in a course if you choose not
to attend the class once you are enrolled.

Student Grievance Procedures

Procedures for student grievances are found in Title V, Rules on Student Services
and Activities, of the university’s Handbook of Operating Procedures.

In attempting to resolve any student grievance regarding grades, evaluations, or

other fulfillments of academic responsibility, it is the obligation of the student
first to make a serious effort to resolve the matter with the instructor, supervisor,
administrator, or committee with whom the grievance originates (hereafter called
“the respondent”). Individual faculty members retain primary responsibility for
assigning grades and evaluations. If the matter cannot be resolved at that level,
the grievance must be submitted in writing to the respondent with a copy of the
respondent’s School Dean. If the matter is not resolved by the written response
provided by the respondent, the student may submit a written appeal to the School
Dean. If the grievance is not resolved by the School Dean’s decision, the student
may make a written appeal to the Dean of Graduate or Undergraduate Education,
and the deal will appoint and convene an Academic Appeals Panel. The decision
of the Academic Appeals Panel is final. The results of the academic appeals
process will be distributed to all involved parties.

Copies of these rules and regulations are available to students in the Office of the
Dean of Students, where staff members are available to assist students in
interpreting the rules and regulations.

Incomplete Grade Policy

As per university policy, incomplete grades will be granted only for work
unavoidably missed at the semester’s end and only if 70% of the course work has
been completed. An incomplete grade must be resolved within eight (8) weeks
from the first day of the subsequent long semester. If the required work to
complete the course and to remove the incomplete grade is not submitted by the
specified deadline, the incomplete grade is changed automatically to a grade of F.

Disability Services

Course Syllabus Page 10

 The goal of Disability Services is to provide students with disabilities educational
opportunities equal to those of their non-disabled peers. Disability Services is
located in room 1.610 in the Student Union. Office hours are Monday and
Thursday, 8:30 a.m. to 6:30 p.m.; Tuesday and Wednesday, 8:30 a.m. to 7:30
p.m.; and Friday, 8:30 a.m. to 5:30 p.m.

The contact information for the Office of Disability Services is:

The University of Texas at Dallas, SU 22
PO Box 830688
Richardson, Texas 75083-0688
(972) 883-2098 (voice or TTY)

Essentially, the law requires that colleges and universities make those reasonable
adjustments necessary to eliminate discrimination on the basis of disability. For
example, it may be necessary to remove classroom prohibitions against tape
recorders or animals (in the case of dog guides) for students who are blind.
Occasionally an assignment requirement may be substituted (for example, a
research paper versus an oral presentation for a student who is hearing impaired).
Classes enrolled students with mobility impairments may have to be rescheduled
in accessible facilities. The college or university may need to provide special
services such as registration, note-taking, or mobility assistance.

It is the student’s responsibility to notify his or her professors of the need for such
an accommodation. Disability Services provides students with letters to present
to faculty members to verify that the student has a disability and needs
accommodations. Individuals requiring special accommodation should contact
the professor after class or during office hours.

Religious Holy Days

The University of Texas at Dallas will excuse a student from class or other
required activities for the travel to and observance of a religious holy day for a
religion whose places of worship are exempt from property tax under Section
11.20, Tax Code, Texas Code Annotated.

The student is encouraged to notify the instructor or activity sponsor as soon as

possible regarding the absence, preferably in advance of the assignment. The
student, so excused, will be allowed to take the exam or complete the assignment
within a reasonable time after the absence: a period equal to the length of the
absence, up to a maximum of one week. A student who notifies the instructor and
completes any missed exam or assignment may not be penalized for the absence.
A student who fails to complete the exam or assignment within the prescribed
period may receive a failing grade for that exam or assignment.

If a student or an instructor disagrees about the nature of the absence [i.e., for the
purpose of observing a religious holy day] or if there is similar disagreement

Course Syllabus Page 11

 about whether the student has been given a reasonable time to complete any
missed assignments or examinations, either the student or the instructor may
request a ruling from the chief executive officer of the institution, or his or her
designee. The chief executive officer or designee must take into account the
legislative intent of TEC 51.911(b), and the student and instructor will abide by
the decision of the chief executive officer or designee.

These descriptions and timelines are subject to change at the discretion of the
Professor.

Course Syllabus Page 12

 WASTE HANDLING IN THE ORGANIC CHEMISTRY LAB

The following procedures must be observed by all students. Failure to comply adds to the workload
of personnel involved in the organic lab operations and may actually result in injury to others. Your
cooperation and your feedback are greatly appreciated.

1. CHEMICAL WASTE

Most of the chemical waste generated in the organic lab falls into four categories:

a) Organic solids and liquids

b) Aqueous solutions
c) Inorganic solids
d) Substances that require special handling

Accordingly, there will always be at least three labeled beakers in the waste hood, one for each of the
first three categories. Students must place all organic solvents and solids in the beaker labeled
“organic waste.” Organic substances are those containing carbon in their structure. Examples of
organic waste are solvents such as methylene chloride, ether, or alcohols. Organic solids include
sulfanylamide and caffeine.

Many experiments result in formation of an aqueous layer that is not used and must be discarded.
Accordingly, this and any other solutions involving water as the solvent must be placed in the beaker
labeled “aqueous waste.”

Finally, some substances fall into the category of inorganic solids. Inorganic substances are those
that do not contain carbon in their structure. Examples of inorganic solids commonly handled in the
lab are sodium chloride, sodium sulfate, calcium chloride, alumina, and silica gel. These substances
must go into the beaker labeled “inorganic solids.”

The last group is comprised of substances that require special handling. Instructions for the safe
handling of this waste should be given as part of the experiment in which they are used, and a waste
container should be provided for those experiments. Examples are insoluble organics such as Nylon,
concentrated inorganic acids, and TLC plates. If you have waste that does not fit into any of the first
three categories and/or are not clear as to how to handle it, please ask your instructor.

MISPLACED WASTE CREATES BIG PROBLEMS FOR THE PEOPLE WHO MUST HANDLE IT AFTER THE
STUDENTS LEAVE THE LAB. IF IN DOUBT, PLEASE CONSULT YOUR INSTRUCTOR RATHER THAN
CARELESSLY DUMPING WASTE INTO THE WRONG CONTAINERS.

2. BROKEN GLASS AND SHARP OBJECTS

These two types of waste require separate containers. Receptacles for broken glass are placed at
strategic points in the organic labs (see picture below). Unfortunately, some students confuse these
containers with trash cans. BROKEN GLASS RECEPTACLES ARE NOT TRASH CANS. Please do not
place anything in these boxes other than glass. The only exceptions to this rule are Pasteur pipettes
that may contain silica gel, alumina, or cotton inside. You can place these pipettes into the broken
glass box without having to empty them first. However, the rubber bulbs that are commonly used
with such pipettes are not disposable. Please do not dump them into the trash can or the broken
glass boxes.
 A BROKEN GLASS RECEPTACLE IS NOT A TRASH CAN

Sharp objects also require a special container. This container is typically a red plastic box located in
the waste hood. The container is designed so that objects can go in easily, but cannot be taken out.
Examples of sharp objects commonly used in the organic lab are disposable syringe needles. Please
place such items in the sharp objects box.

A TYPICAL SHARPS CONTAINER

3. REGULAR TRASH

There are regular trash cans placed at specific locations in the organic lab. Unfortunately, certain
regulations limit the amount of trash cans that can be placed in each lab. As a result there might not
be one handy when you need it. This in turn makes it tempting to place trash in broken glass boxes.
Please take the time to locate a regular trash can and place items such as paper, gloves, and other
harmless waste in them, even if you have to walk a little longer.

EXAMPLES OF TYPICAL TRASH CANS

PLEASE DO NOT PLACE SHARP OBJECTS OR BROKEN GLASS IN TRASH CANS. THE TRASH BAGS
EASILY PUNCTURE, WHICH POSES A HAZARD TO THE JANITORIAL PERSONNEL WHO HANDLES THEM
4. DISPOSABLE VERSUS NONDISPOSABLE ITEMS

Most of the items of routine use in the organic lab can easily be identified as either disposable or not
disposable. However there are certain items which for some reason seem to fall into a limbo zone.
Examples of these are rubber bulbs. These items (shown below) are not disposable.

ALTHOUGH CHEAP LOOKING, THESE ITEMS ARE NOT DISPOSABLE

Test tubes, on the other hand, are disposable. However, before placing those into the broken glass
container make sure to remove any chemicals from the tube. IT WOULD BE A GRAVE OFFENSE TO
PLACE TEST TUBES WITH CHEMICALS IN THE BROKEN GLASS BOX.

BELIEVE IT OR NOT, TEST TUBES ACTUALLY LOOK LIKE THIS AND THEY ARE DISPOSABLE

Centrifuge tubes, on the other hand, are not disposable. But of course, you already knew this
because it would cost you money to throw them away. Hmm, maybe that would be a good way to deal
with rubber bulbs as well…

To recap, here is a list of a few behaviors which, if observed in the lab, may actually carry a curse with
them:

a) Putting chemical waste into the wrong containers

b) Throwing away rubber bulbs
c) Placing anything in the broken glass box other than glass
d) Placing glass or chemicals in the regular trash cans
e) Leaving trash anywhere in the lab where it does not belong, including bench tops, the
weighing balance area, or the hoods where you work.

THANK YOU VERY MUCH FOR YOUR CONTRIBUTION TO MAKING THE ORGANIC LAB THE
MOST PLEASURABLE PLACE TO BE ON THE UTD CAMPUS !
 CHEM 2123 and 2125 – Organic Chemistry Lab I and II

GUIDELINES FOR WRITING LAB REPORTS

INTRODUCTION

Writing reports in organic chemistry lab may differ from the way it’s done in general chemistry. One
goal of this course is to introduce you to the record keeping methods used in research labs. Such
methods are designed to organize experimental data in a format similar to that required for publication
in major scientific journals. Here are some important considerations that apply in research settings.

1. Your work is unique, meaning that you might be the only person performing certain experiments.

2. Research is an ongoing process. The projects assigned to you will likely continue after you leave.
People assigned to those projects will need to access your records for reference, or to attempt to
reproduce work you did. Permanence is a characteristic of properly kept research records.

3. It is therefore important to follow guidelines for clear writing. In addition to writing legibly, you should
use permanent ink. A ballpoint pen is adequate for this purpose, but a pencil is obviously not.

4. Write your records by hand, either while conducting the experiment, or immediately afterwards. This
is important to avoid forgetting important details. You will make mistakes, but that is less important
than recording data while it’s still fresh in your mind.

5. Mistakes are not to be erased. A “mistake” might turn out to be important information later. You and
others must be able to read what you wrote. If you make a mistake, draw a line across the text, but
make sure it remains legible, like this.

6. Remember: your lab notebook is the first line of documentation that exists of your experiments. It is
important that this information be as fresh and accurate as possible. Don’t worry if it’s imperfect. You
will have occasion to produce a formal, well written report later. It may be a thesis or a scientific
publication, but it will likely bring together several experiments with a common theme. Your lab
notebook will be the primary source of data for such publication.

7. Do not write on loose sheets of paper, or even in spiral notebooks from where pages can be torn. Use
a hardbound notebook, with numbered pages, that makes carbon copies as you write. That makes it
easy to spot missing pages, and it gives you two sets of records that you can keep in separate locations
in case one of them gets lost or damaged.

8. Do not tear pages from a research notebook unless they’re damaged or threaten the integrity of the
notebook (by catching acid, for example). If both original and copy get damaged, try to reproduce their
contents the best you can, with a note explaining the absence of the originals.

TYPES OF REPORTS HANDLED IN THESE COURSES

In the organic chemistry lab course there are two types of reports, which are all graded on a 100 point
scale. One type comprises what’s commonly known as “lab reports,” that is, records referring to
experiments performed in the lab. The other type refers to special assignments that are completed
outside the laboratory. The format and contents of special assignments depends on their nature. They
are specified in the syllabus, or at the time the assignment is made. Examples are the MSDS assignment
in organic lab I, or the Chemical Literature assignments in organic lab II.

Lab reports, on the other hand, have a set format. They can be or two kinds, depending on whether they
refer to experiments involving physical operations or chemical preparations (synthesis).
 2
LAB REPORTS FOR PHYSICAL OPERATIONS, OR TECHNIQUE EXPERIMENTS

This type of report refers to lab work whose main objective is to learn, demonstrate, or perform a
physical operation. Physical operations do not change the chemical nature of the substances involved.
They are typically conducted as part of a synthesis and are frequently of two types:

1. Purification techniques, or separations. These operations are designed to isolate a pure

substance from a mixture. Examples are crystallization, extraction, and distillation.
2. Characterization techniques. These operations are designed to return information that can be
used to identify a substance. Examples are the determination of physical constants such as
melting point, boiling point, or density, and instrumental techniques such as infrared (IR)
spectroscopy. Sometimes these techniques are referred to as analytical techniques .

LAB REPORTS FOR CHEMICAL PREPARATIONS, OR SYNTHESIS

This type of report refers to experiments whose main goal is to prepare a pure substance from specific
starting materials. This necessarily involves a chemical transformation, or reaction. In the simplest
case, there is only one step. The starting materials are combined and a product forms. This product is
isolated, purified, and characterized, producing the final outcome of the experiment. In a multistep
synthesis, the product of the first step is used as a starting material in a second step, and so on, until a
final product is obtained. No multistep synthesis are performed in organic chemistry lab I. Some two
step synthesis are performed in organic chemistry lab II.

FORMAT FOR LAB REPORTS

The general format for most reports is the same and is given below. Specific differences with examples
will be discussed later. In addition to the heading showing the title, date, and your name, you are
expected to include the following items in your lab notebook. All reports are graded on a 100 point scale
with the following distribution.

1 INTRODUCTION (objectives and tables) 20 points

2 EXPERIMENT OUTLINE (brief list of steps) 10 ”
3 OBSERVATIONS OF PHYSICAL CHANGES 20 ”
4 TABLE OF RESULTS (with supporting materials) 20 ”
5 RESULTS, DISCUSSION, and CONCLUSIONS 20 ”
6 ASSIGNED PROBLEMS (from the textbook) 10 ”

The first two items of the report (introduction and experiment outline )
should be written in your notebook prior to the experiment.

1. Introduction – Depending on the type of experiment being performed, this section may contain the
items shown below. The first two are relevant to all experiments. The last two are relevant to some
experiments. If you cannot find some of the required information in textbooks and common sources
such as MSDS or the Aldrich catalog, simply indicate so. If the information is not pertinent, write N/A
for not applicable. If it is unknown, indicate so.

a. Objectives of the experiment

b. Table of physical constants
c. Relevant chemical equations and reaction mechanisms (in the case of synthesis)
d. Diagram or sketch of setup used (if it serves for illustration purposes or to enhance clarity)
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Objectives can be learning objectives and/or experimental objectives. For example, in a crystallization
experiment the learning objective is to illustrate the technique of crystallization by having the student
perform the steps involved. But the experiment objective is to purify a substance by crystallization and
prove that it is reasonably pure by its melting point.

A table of physical constants should include the following for every major chemical used in the
experiment: chemical structure , molecular weight , boiling and/or melting point , density, and
safety hazards such as flammability and toxicity . Under safety hazards, indicate the source of
information with a footnote (Aldrich catalog, MSDS, etc.). If the substance poses special hazards, make
a note under the table regarding safe handling and emergency procedures in case of contact. An MSDS
must always be consulted before handling hazardous substances .

Synthesis reports must include chemical equations. Include molecular mass and amounts used, in
grams and in moles, for each reactant. This will enable you to find out which is the limiting reagent
when the time comes to calculate the percent yield of the product. If the mechanism of the reaction is
known (given in your book, or during class), make sure to include it too.

A picture can save you many words. If it serves an illustrative purpose, the introduction can also include
a diagram or sketch of the setup used, such as a distillation apparatus. It doesn’t have to be a work of
art and it doesn’t need to be done every time a distillation is performed. If you do distillations again,
simply refer the reader to the first experiment where the setup was used, or to a source such as an
article or book.

Examples of different parts of a lab report are given at the end of this guide and in your textbook.

2 and 3. Experiment outline and Observations of physical changes – The split page format should be
used at this point. If your notebook does not already have a vertical line that divides each page in half,
draw one when you start section 3. On the left side, give a list of the steps that the experimental
procedure calls for (part 2). On the right side, record any physical changes that occur as you perform
those steps (part 3). For example, when you combine two substances, a change in color might occur,
the solution might get hot, or bubbles might form. This provides readers with landmarks to look for if
they try to reproduce your work.

The list of steps provides a handy, quick reference that keeps you from having to use the book or ask
your instructor what to do every time you finish a step. The level of detail in this section should be
subordinate to your needs and learning style, but it should be no longer than a page or two, and it
should not require inordinate amounts of time to write.

4. Table of results and supporting materials – This is similar to the table of starting materials but it
shows data that pertain to the products or results of the experiment. Supporting materials is any
physical evidence such as spectral charts, chromatograms, or instrument readouts. Sometimes there
are no supporting materials. For example when you take a melting point you simply read it from a
temperature scale, but the instrument doesn’t produce any chart or physical record of it. On the other
hand, when you run a chromatographic plate, you have the plate as evidence of the results.

A report referring to a physical operation should contain the parameters indicative of the success of
the operation. For example, in a purification procedure, give the parameters that indicate the degree of
purity of the substance (e.g. melting point, IR spectrum). Also give the percent recovery of pure
substance relative to impure substance, complete with relevant calculations.

A report referring to a reaction or synthesis should contain any parameters that indicate you obtained
the expected product. Examples are melting point or spectral data. Include the percent yield, with
relevant calculations (make sure that you know how to identify the limiting reagent when one of the
reactants is in excess).
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5. Results, discussion, and conclusions – This is where subjective interpretation comes in. By now you
have gathered a certain amount of data, figures, charts, etc. It is time to interpret what that information
means. For example, is the melting point obtained close to the expected value? If not, what could
possibly be the reason? What information can be gathered from a chromatogram or a spectral chart?
Does it support the results you expect to obtain?

Understandably, students find this the hardest part of the report to write. If you experience this type of
difficulty, it might help you to go back and retrace all the parts of the lab report. Start with the
introduction. Were the objectives and goals of the experiment met? If not, why not? This is where you
start thinking about possible sources of error.

Types of error can be systematic or random. Systematic error is a consistent error that can be detected
and corrected. This occurs most commonly when using precision equipment that requires calibration,
such as thermometers, burets, and pH meters. Miscalibration can give rise to systematic error. Random
error results from limitations in our ability to make physical measurements. For example, when reading
a scale, different people might report slightly different results due to their subjective interpretation of
the values they read between marks. Random error can also result from variations in an instrument’s
performance inherent in its physical makeup. For example, electrical noise might produce slightly
different readouts at different times. Random error cannot be eliminated, but it can be reduced by
improving the experiment, or by using better equipment.

Next, you might want to go to section 3 and see if you can provide explanations for at least some of the
physical changes observed here. For example, in a Grignard reaction, a change in color is observed as
the reaction proceeds. This might be explained by invoking formation of an intermediate in the reaction
mechanism. When a step calls for neutralization of excess acid with sodium bicarbonate, formation of
bubbles is observed. This can be explained if you know that this reaction produces carbon dioxide gas.
As you can see from these examples, many observations can be explained if you have a good
understanding of the theory of the experiment .

The last section to draw from is section 4, where you have presented all the raw data that you gathered
during the experiment. The term raw data refers to information that has not yet been organized or
interpreted. You can start by answering the question, were the outcomes of the experiment as
expected? If yes, what evidence supports this conclusion? For example, was the melting point within the
range reported in the literature? If not, what does the evidence indicate that might have happened
instead? Maybe the spectrum of what you think is a product really corresponds to the spectrum of the
starting materials, indicating that there was no reaction. Maybe it is a mixture of products and starting
materials, indicating partial reaction. Maybe it is the spectrum of a byproduct, indicating that the
conditions of the experiment favored formation of a product other than the expected one.

If the experiment worked as expected, there is little need for superfluous elaboration in this section.
Remember that the quality of a report does not correlate with the amount of writing done. It correlates
with the substance and the clarity of the material presented.
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EXAMPLES OF PORTIONS OF LAB REPORTS

EXAMPLE 1: AN INTRODUCTION TO A REPORT OF A PHYSICAL OPERATION

In this example, the students will perform a physical operation known as crystallization. This operation
is intended to purify solids containing small amounts of impurities.

INTRODUCTION. In this experiment acetanilide will be purified by crystallization from water.

The learning objectives are to learn the applications of this technique and its execution, and to
learn how to take a melting point. The expected outcome is to obtain a pure substance from an
initially impure sample and to demonstrate its purity by recording its melting point.

TABLE OF PHYSICAL CONSTANTS

Substance Structure M.W. m.p. b.p. Density Safety

(oC) (oC) hazards*
O
Acetanilide H 135.17 117-115 -- -- Toxic,
N CH3
Irritant

Water H2O 18.02 0 100 1.00 nontoxic

* Source: Aldrich catalog, 2003-04.

No highly toxic substances are handled in this experiment. In case of skin contact with
acetanilide, wash affected area with plenty of soap and water.

EXAMPLE 2: AN INTRODUCTION TO A REPORT OF A CHEMICAL REACTION, OR SYNTHESIS

In this example, the students will prepare 1-bromobutane from 1-butanol in an acid catalyzed reaction.

INTRODUCTION. In this experiment 1-bromobutane will be prepared from 1-butanol in an acid-

catalyzed Sn2 reaction. The main learning objective is to illustrate a synthetic application of
the Sn2 reaction. The expected outcome is to obtain a reasonably good yield of product with
minimal formation of side products such as alkenes arising from elimination reactions.

CHEMICAL EQUATIONS
CH3CH2CH2CH2OH + NaBr + H2SO4 CH3CH2CH2CH2Br + NaHSO4 + H2O
sodium sulfuric sodium
1-butanol bromide acid 1-bromobutane bisulfate

M.W. 74.12 102.9 98.08 137.03

amounts .185 g .300 g .250 mL .342 g (342 mg)

used (185 mg) (300 mg) (.460 g, or ((theoretical)
460 mg)
mmoles 2.5 (theoretical)
2.50 2.92 4.69
used
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CALCULATIONS

Calculating mass of sulfuric acid from its measured volume

Density = mass (g) / volume (mL)  mass = density X volume

mass = 1.84 g/mL X .25 mL = 0.46 g
Calculating mmoles from the mass of the substances

Moles = mass (g)/M.W. (g/mol)

Moles of 1-butanol = .185 g /74.12 = .0025 moles = 2.5 mmoles

Moles of NaBr = .300 g /102.9 =.00292 g = 2.92 mmoles

Moles of H2SO4 = .46 g /98.08 = .00469 moles = 4.69 mmoles

Calculating theoretical yield of product

The limiting reagent in this reaction is 1-butanol. The balanced equation shows that one mol of
1-bromobutane is obtained for every mol of 1-butanol used. Since we are starting with 2.5
mmoles of 1-butanol, then the theoretical yield of 1-bromobutane is also 2.5 mmoles, or .342 g.

You must note the following: (a) When handling very small amounts of substances it is more convenient
to use millimoles (mmoles) instead of moles. (b) We are mainly concerned with reporting the properties
of organic products such as 1-bromobutane, and not inorganic products such as sodium bisulfate.
Inorganic products are typically separated and discarded. (c) Not all reagents are present in equimolar
amounts. In such reactions, the limiting reagent is the one present in the smallest amounts, such as 1-
butanol in this example.

TABLE OF PHYSICAL CONSTANTS

Substance Structure M.W. m.p. b.p. Density Safety

(oC) (oC) (g/mL) hazards*
1-Butanol CH3CH2CH2CH2OH 74.12 -89.8 117.5 .81 Flammable

Sodium NaBr 102.9 -- -- -- Irritant,

bromide hygroscopic
Sulfuric H2SO4 98.08 -- -- 1.84 Highly
Acid, 98% corrosive
1-Bromobutane CH3CH2CH2CH2Br 137.03 -112 100 – 1.276 Flammable,
104 irritant
* Sources: Aldrich catalog, 2003-04, MSDS.

All substances must be handled in the hood, wearing gloves and eye protection. Avoid contact
with eyes and inhalation. Skin contact procedures for these substances: Wash affected area with
plenty of soap and water. If a skin rash or a burning sensation results, see a physician
immediately. Eye contact with sulfuric acid requires immediate attention. Wash with plenty of
water and see a physician as soon as possible.
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REACTION MECHANISM

The reaction between sodium bromide and sulfuric acid generates HBr. There is a high
concentration of bromide ions in this medium. The first step is a proton transfer to produce the
protonated alcohol with a good leaving group (water). In the second step, bromide ion acts as a
nucleophile to displace the water and form the substitution product.

O
fast
(1) CH3CH2CH2CH2OH + H O S OH CH3CH2CH2CH2-OH2 + HSO4
O
1-butanol sulfuric protonated alcohol bisulfate ion
acid (conjugate acid) (conjugate base)

Sn2
(2) CH3CH2CH2CH2-OH2 + Br CH3CH2CH2CH2Br + H2O
slow

APPARATUS USED

A reflux setup as indicated on p. 210 of the Pavia textbook was used. The only modification was
the omission of the gas trap at the top, since this reaction was conducted in the hood.

EXAMPLE 3: SPLIT-PAGE FORMAT FOR THE EXPERIMENT OUTLINE AND PHYSICAL OBSERVATIONS

In this example, acetylglycine is being prepared by reaction of glycine with acetic anhydride. On the left
column the student shows the experiment outline as a list of steps (part 2). On the right side the
student writes all relevant physical observations made as the steps are followed (part 3).

EXPERIMENT OUTLINE OBSERVATIONS

1. Place 0.10 g glycine in a 5 mL conical vial
2. Add 0.4 mL water and warm slightly to
dissolve
3. Add 0.3 mL acetic anhydride and stir
mixture for about 5 min.
4. Cool mixture in ice bath for about 10 min.
5. Collect precipitate by suction filtration and
wash with a few mL of water.
6. Spread crystals over a piece of filter paper or
watch glass and air dry for about 10 min.
7. Record mass and melting point of product.
…………..
Glycine dissolved after about 20 sec.
The solution remained clear.
White, needle-shaped crystals formed.
…………….
…………….
0.14 g. of solid was obtained, mp = 205-207 o
Possibly still slightly wet.
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EXAMPLE 4: RESULTS, DISCUSSION, AND CONCLUSIONS

In this example, impure acetanlide was purified by crystallization. The percent recovery and melting
point were recorded.

RESULTS, DISCUSSION, AND CONCLUSIONS

The crystallization of acetanilide gave a 52 % recovery. Loss of product during the hot filtration
accounts in part for the low recovery. The melting point of the crystallized product (110-112 oC)
is higher than that of the crude material (105-109 oC), indicating a higher degree of purity.
However, the melting point of the crystallized product is lower than the reported literature value
(113-115 oC), indicating that it is not completely pure. Perhaps presence of residual water
(crystallizing solvent) and error in the melting point determination can account for this.

The conclusion is that the crystallized material was in fact acetanilide, based on its melting
point, but it was not highly pure. A second crystallization should produce a fairly pure
material, but it would also decrease the % recovery.