CHEM 332.003 and 004 Lab Syllabus
Spring 2014
Temporal and Spatial Data
Section
Day
Time
Place
003
M
12:30 - 04:20 PM
SM 541, 591
004
W
12:30 - 04:20 PM
SM 541, 591
The all important GRADING info
All laboratory experiments must be performed and a report for each experiment must be handed
in; one or more missing lab reports will result in your laboratory grade being an F. Laboratory
reports must be submitted on time; no late reports will be accepted.
Laboratory reports will be graded A, B +, B, etc. At the end of the semester, the letter grades will
be translated into numerical equivalents using the middle points of my grade scale (i.e. A = 92.5,
B- = 79.5, and so on).
NOTE : you must attain a grade of C or better in both the laboratory and the lecture portion of
the course in order to attain a passing grade.
Scope:
This laboratory is an adjunct to the second semester Organic Chemistry course. It is intended to
further develop the laboratory technique, this time on a microscale, the preferred contemporary
methodology for organic and biochemical experimentation. Primary emphasis will be on advanced
organic syntheses, including multi-step transformations, and on the use of 13C-NMR in
identification of organic molecules.
Laboratory Materials:
Handouts: (available from
http://pages.towson.edu/jdiscord/WWW/332_Lab_Info/332_LabPacketExpts.htm)
Notebook: 4 x 4 Quadrille Rule, 81/2 x 11" spiral bound notebook, National Number 43-647. No
alternative notebook can be used.
Safety goggles. Must be OSHA or ANSI approved. Safety goggles will be sold by the Student
Affiliates of the American Chemical Society during the first lab period, or they may be purchased
from the University Bookstore.
Laboratory Records.
Laboratory report - One week after you have completed each experiment you will be required
to turn in the following (details are given below the list):

Lab Report (computer generated from a template at
http://pages.towson.edu/ryzhkov/stud.html)

Carbon copy of lab notes with supporting data sheets from spectrometer(s) or
chromatograph

Products, only for some experiments.
A. Structure of the Lab Report

Abstact:
When the experiment is completed, you will make a summary or abstract of the experiment
(1-2 brief paragraphs). DO NOT PLACE ACTUAL EXPERIMENTAL DATA INTO THE
ABSTRACT! Rather, it should inform the reader about the exact laboratory techniques utilized in
an experiment, the reason for doing the work, and the most pertinent results obtained. If the
experiment involves a synthesis or a reaction in general, the abstract must contain an overall
reaction equation, and a reaction mechanism!
The abstract need not be in your notebook. By all means, avoid phrases such as: "I placed the
compound into a beaker and stirred with a glass rod until it dissolved..."

Data:
Following the abstract you will place the data part of the lab report. By all means, place all the
data entries into a well-constructed table, do not merely list them one after another on a
page. The data section should separated into two parts: 1. the compounds and 2. other.
Part 1 includes the molecular formula, molecular weight, actual weight (in grams or milligrams) or
volume, densities (when applicable and if available), and molar amounts for every chemical,
reagent or product used in the lab. Obviously, if the chemical is used as the solvent, you need
not calculate molar amounts. The same applies to the solids used to dry organic phases etc.
Part 2 contains other data such as the reaction mixture stirring or heating times, RPM values used
in centrifugation, addition times of reagents, mL of distillates, temperatures, heights or areas of
peaks in GC traces, melting or boiling points etc. NOTE! EVERY NUMBER YOU
MEASURED OR OBSERVED IN THE LAB MUST BE RECORDED AND REPORTED.
If spectroscopic data is analyzed, the results must be placed into a separate table(s). For the IR
data, the table must have columns for the resonant frequency, size of the band (small, medium,
weak), and the assignment of the vibration corresponding to the IR band(s). The NMR data table
must include: the ppm shift of the signal, multiplicity (splitting pattern), area (as determined by the
electronic integrator etc.) and the assignment of the resonance. The MS data table must include the
fragments with their structure and mass and M+ cluster with all assignments.

Calculations:
In this part of the report, you must include all the relevant calculations that you performed in
order to process the data acquired in the lab. These will include: calculations of molar amounts,
identification of limiting reagents, yields of products, concentrations, weights derived from
densities and vice-versa, etc. You must show the theoretical formula used in the calculation,
followed by the expression listing the actual experimental numbers used.
As an example, when calculating the molar amount of a substance, you will first write:
molar amount = (weight in grams / molecular weight )
followed by the actual numbers, i.e. = ( 0.234 g / 134.5 g/mol ) = 1.74x10 -3 moles.
Please, make sure that you observe significant figures and spell the physical units such as mL, mg
etc. correctly.

Conclusions:
This is, by far, the most important part of the lab report. In this section, you must clearly state the
conclusions of the experiment. What is the nature of the unknown? How did you identify the
substance? Is there still any ambiguity left? What was % yield? If it was small, what are the
relevant errors? Make only those conclusions, supported by the data. List all the problems
encountered while conducting an experiment. I will check the copies of the lab notebook against
this section.
B. Laboratory notebook
You are to treat your laboratory notebook as if it were the only record anywhere of how to do any
one of your experiments. Pretend that you are doing research and that no one has ever done this
experiment before. The notes you take should be sufficient so that anyone (including yourself 10
years from now) can take your notebook and repeat the experiment using your notes as the only
guide.
The lab notebook should have carbon papers. As you will work in lab, you will keep carbon copies
of your work; you will turn these in to me as part of your report. Page 1 will be reserved for table
of contents. Each new experiment will start on a new page and the date will be entered each day
you work in the lab. When you come to lab, you should have entered in your notebook the title,
data and, where appropriate, balanced equation and calculations only. In most cases the title will
serve as an "introduction".
As you work in lab, you should write in your notebook on the right hand page everything you do
and see, taking carbons as you go. Any planning notes, notes from lab lecture, rough calculations,
rough weights should be entered on the left hand side (no carbons). Lab notes must not be taken
on the scraps of paper or in other notebooks. I will remove those when I see them. Write
everything you do in your own words as you do it; do not copy text instructions. No laboratory
notebook entries, except calculations should be done outside the lab. Include ONLY what you did
and observed, that's the most relevant part of your lab experience.
Each chemical transformation that you perform needs to be documented, so that it is clear to the
reader of your report that you have accomplished the transformation. A melting point and IR
spectrum should be determined for each starting material and product (boiling points may be
obtained during distillation or in a separate experiment).
Observations and procedures should be completely integrated since you will write things as they
happen; be sure to record any errors, repeats etc. since I'll remember them. No record should ever
be removed from the notebook. If you did something wrong, the notes should remain with a clear
notation that this was an error. The most important aspect of your lab notebook is its value as a
complete and accurate record of the experiments.
At the end of the experiment, you should do any calculations and make any comments about
errors. Explicit conclusions may consist of the yield, physical properties and identity of the
product or an unknown. Spectroscopic data should be labeled as such and attached to your report.
Your conclusions for the experiment should include interpretation of the data you have collected,
especially chromatographic and spectroscopic.
C. Products
For some experiments you will turn in your products. The products may be graded for yield and
purity and will count no more than 10% of the grade of the experiment. No credit will be given for
inadequately identified materials. Each vial, containing a product, must be labeled with the
following:






Your name, course and section
Name or number of compound
Number of grams
% Yield
Melting range or boiling range
Instructor's name
Additional References.
These additional books may be of use to you and may be found in the library (reference, faculty reserve
room or stacks), Chemistry Tutoring Center or in the laboratory.
•
Spectrometric Identification of Organic Compounds by Robert M. Silverstein,
Francis X. Webster, and David Kiemle (2005)
•
CRC Handbook of Chemistry and Physics, 88th Edition by David R. Lide (2007)
•
CRC Handbook of Tables for Organic Compound Identification Third Edition by
Zvi Rappoport (1980)
•
Handbook of Organic Chemistry, J. A. Dean, McGraw-Hill, New York (1987)
SCHEDULE OF LABORATORY
EXPERIMENTS
Week
Title
1/27
No Labs – Add/Drop period – Optional Intro, Review of Basics, if
desired
2/3
Spectroscopy Test (20% of Lab Grade), IR Review
2/10
Proton NMR Review, Review EA/MS, Introduction, Safety
Discussion, Locker Check-In
2/17
Expt 1: Reduction of Vanillin
2/24
Expt 2: Oxidative Cleavage of Cyclohexene
3/3
Experiment 3a: Synthesis of Lidocaine, part A
3/10
Experiment 4: Grignard Reaction
3/17
Spring Break – No Classes
3/24
Expt 5:
13
C NMR
3/31
Expt 5:
13
C NMR
4/7
Expt 5:
13
C NMR
4/14
Expt 6: Esterification - Isobutyl Propionate
4/21
Expt 7: Friedel-Crafts Alkylation of p-Xylene
4/28
Follow-up Discussion of FC results (if desired)
5/5
Lab Assessment Exam (50 minutes); Locker Clean Up and
Check-out