Borough of Manhattan Community College Organic Chemistry

PREFACE

This manual is provided free of charge to all BMCC students enrolled in a two-semester course of
Organic Chemistry. It was created with the purpose of helping and instructing at the college level with
material readily available. Most of the commercial manuals have been written with an overwhelming
amount of information which tends to confuse and frustrate the student. The background material
provided here is meant to confer enough details to understand the experimental part while keeping the
course at the proper level. Any experiment can be performed in a single session. Although, for different
reasons, certain experiments might have to be carried out and finished in the next laboratory period.

Mistakes, omissions, language, misused technical words, mis-assigned figures, and other errors
might be found across the manual. Please bear with them and inform your instructor so this manual can
be improved. If you would rather send me an e-mail, I would really appreciate it.

Carlos Alva, Ph.D.

Department of Science
E-mail: cwalva@hotmail.com

-i-
Borough of Manhattan Community College Organic Chemistry

- ii -
Borough of Manhattan Community College Organic Chemistry

LABORATORY SAFETY

All the Organic Chemistry students have one-year experience of General Chemistry and they are
aware of most of the dangers present in the chemistry laboratory. In the organic chemistry laboratory,
they are going to be exposed to organic materials which present a different danger from the inorganic
ones. Most of the organic compounds have a lower melting and boiling point than inorganic salts and
they can be easily inhaled, ingested, or absorbed through the skin. Despite the many hazards involved,
these same materials can be easily handled when the student is well informed and prepared to
manipulate and use them. Safety information can be obtained from a variety of sources. After consulting
and developing the experiment, the most important safety information is provided at the beginning of the
experimental part. But just because this information is provided, it does not mean that the student should
not go to the library and read about the physical and chemical properties of these materials. At this point,
the student is encouraged to do so and eventually, it will be reflected in the preliminary write-up needed
for each experiment. At the first meeting of the organic lab, the safety procedures will be discussed by
the instructor and as the precautions change with each experiment, the student must be prepared before
hand. Probably, the best way to enjoy your laboratory work and avoid accidents is by knowing what to do
and expect. Do not go to perform an experiment without preparation. Your instructor will make sure that
you know what you will be doing and if you do not, be prepared to leave the laboratory.

At the beginning of your work, make sure that all the chemicals, glassware, and instrumentation
are ready. Do not use any excess amount of chemical. If the procedure requires 10 mL of a liquid, get
only what you need. Sometimes, the student collects a tenfold of material and then at the end of the
experiment, this excess goes into the garbage or down the drain. Well, you should know that only water
and ethanol can go down the drain. Any other material must be collected in the proper receptacle.
Halogenated chemicals are collected in a waste jar labeled FOR HALOGENATED WASTE ONLY. Solid
materials go into their proper receptacle labeled FOR SOLID WASTE ONLY. Usually, the waste jars
are located in the hood at the far end of the laboratory. If there is an acid spill, neutralize it with either
solid or an aqueous solution of sodium bicarbonate. Broken glassware must go into the blue box labeled
BROKEN GLASS ONLY. If working with a flammable material, make sure that no Bunsen burners or
any other device that produces a flame is ON. If you believe that someone is not taking the proper
precautions and might produce a hazard to other students or himself/herself, please inform your
instructor, as you will be doing everybody a favor.

- iii -
Borough of Manhattan Community College Organic Chemistry

LABORATORY NOTEBOOK

The laboratory notebook is to be a complete, original record of the experimental work. The
requirement is that you use a bound composition notebook that can be purchased for 50 cents to a dollar
utmost. You should not use loose leaves or spiral notebook for recording laboratory work. The report
must be sufficiently complete and well-organized so that anyone who reads it can understand, follow, and
repeat the experiments.

Please leave the first eight pages for the table of Contents and any references that you may find on
the Web relevant to the experiments. You might want to also use these pages to record any abbreviations
that you used in your notebook.

Number the pages in your notebook. Start recording your fist experiment on page 9. Use the even
numbered pages for making a sketch or calculation as you progress through the experiment. Odd
numbered pages are used for recording your actual experiment.

The notebook consists of the following:

1. A Table of Contents on the first pages,

2. A Reference section consisting of one or two pages listing all the reference books used as
source of information. It must follow the table of contents,
3. The preliminary write-up, consisting of the aim of the experiment, chemicals needed,
apparatus needed, and any theory related to the experiment
4. The actual experiment, where you write down the steps as you carry out the experiment
5. Next, in the discussion section make sense of your results you obtained. Finally, follow that by a
brief conclusion.

Laboratory notebook write-up.

As indicated in each experiment, it must be written in your notebook before you begin the
experiment.

This write-up consists of the following:

(a) An introduction which states the objective,

(b) A balanced chemical equation describing the experiment in one glance, including molecular

- iv -
Borough of Manhattan Community College Organic Chemistry

weights, amounts to be used (in grams and millimoles) followed by the calculation of the
theoretical yield. Sometimes, a flowchart of the overall experiment is helpful.

(c) A description of the procedure, which may be identified by a reference to the manual (author, title
of book, publisher, edition, and pages containing the information) or any other source. This
reference must be recorded fully on the reference section for the first time and for subsequent
referrals, mention of the name of the author and the pages is enough, and

(d) A list of physical properties, hazards and toxicities of the compounds involved and any other data
required by the experiment.

Reference books.
The following reference books will be available to you:

1. The CRC Handbook of Chemistry and Physics published by the Chemical and Rubber Company.
This handbook contains a wealth of information with the physical and chemical properties of
inorganic and organic compounds,

2. The Aldrich Catalog of Fine Chemicals, published by Aldrich Chemical Company, listing
thousands of inorganic and organic compounds, and

3. The Merck Index containing description of medical and pharmaceutical important organic
compounds.

The actual experiment.

As you conduct the experiment you must write a short description of the actual procedure that
you followed including all observations. All data are to be recorded at the time they are observed or
obtained. This includes weighing, boiling and melting points, observations of results, and conclusions.
No separate pieces of paper are to be used for recording data to be transcribed later. If you made a
mistake, record it. You will not be penalized for recording a mistake but you will be for not recording as
you carry out the experiment. The notebook should be neat but this is less important than having it is a
complete, original record. Copying data is a waste of time and leads to copying errors. The record made
at the time of the observation is the important record. If changes or corrections are to be made, the
material considered wrong is to be canceled by drawing a line through it. The revised material is then to
be added. It may be necessary to refer to the record to determine how an experiment might best be
revised or interpreted and for this purpose the record at the time of the observation is important. Keep in
mind that all experiments are different and the format must be changed as needed. Although not

-v-
Borough of Manhattan Community College Organic Chemistry

required, a drawing helps to clarify the experimental set-up. Start every experiment on a new page.
Leave the back of the page for calculations and small details. Record your experiment on the front page
only. Make all records in ink. The notebook is a log of your work and should be dated regularly.

The final write-up.

The conclusion and/or discussion can be recorded outside the laboratory period.

This final write-up consists of:

(a) Identifying and providing the supporting data and reasoning for the unknown material provided to
you,

Benzoic acid
o
(b) In Organic 240, you may end up submitting samples after the mp 121-122 C
3.81 g (31 mmol)
experiment is completed. In such cases, the proper way to label is John Q. Student
shown on the right. In any case, labeling is an important point to be CHE 230-151
conscientious about while working in the laboratory. There should
be no un-labelled bottles in the laboratory.

(c) When a thin layer chromatography, gas chromatography or IR analysis is performed, a copy of
the chromatogram or spectrum must be submitted.

(d) During certain experiments, you will synthesize compounds. For those experiments, you have to
report the yield of the reaction in percentage. When you re-crystallize you will need to report
percent recovered.

(e) A discussion of the theory behind the experiment and its relationship to the observed results. If
your own procedure is different from that in the laboratory manual or notes provided to you, tell
exactly how it differs.

It is to be emphasized that your notebook should be up to date at all times during the laboratory
period as your instructor will examine it frequently. At the end of the semester, your notebook must be
surrendered to your instructor who will keep it for one year, as required by school regulations .

- vi -