CHEM 2380, Summer 2014-Study Abroad in Lyon, France
Synthesis Lab I
INSTRUCTOR
Dr. Cameron Tyson
Evans Administration Bldg (Tech Tower), 201
Email: cam.tyson@chemistry.gatech.edu
Ph: 404-894-0418/404-894-7466
RECOMMENED TEXTBOOKS
The Organic Chem Lab Survival Manual by J.W. Zubrick (6th or 7th edition, John Wiley and Sons, ) and
Organic Chemistry by G. Solomons (8th edition) for discussion of the theory (structure, reactivity, mechanism).
SCHEDULE
The course will include twelve 4-hour lecture periods, twelve 50-minute lectures, a lab practicum, and a lab
final exam.
POLICIES, PROCEDURES AND GRADES
GRADES
Lab Reports
Pre-lab/In-lecture quizzes
Reflective essay/wall posts
Lab notebook, safety, technique
Lab practicum and final exam
800 points
60 points
40 points
100 points
200 points
The course will be graded on the basis of 1200 points:
88% (1056 points) will guarantee an “A”
70% (840 points) guarantees a “B”
60% (720 points) guarantees a “C”
50% (600 points) guarantees a “D”
LAB REPORTS
Experiment 1: Synthesis of dibenzilidene acetone (DBA) (100 points- Business Memo report)
The dibenzilidene acetone is obtained by condensation of two benzaldehydes with acetone under basic
conditions. The product is filtered, wash and then recrystallized in ethanol. Concepts/ techniques studied:
mechanical stirring, recrystallization, solid extraction and wash, analyses of melting point, infra-red spectrum of
a solid, NMR 1H, 13C and DEPT135 (theoretical).
Experiment 2: Synthesis of tert-amyl chloride (100 points-Business Memo report)
Tert-amyl chloride is synthesized for 2-methyl-2-butanol by nucleophile substitution (SN1) using concentrated
hydrochloric acid. The product is washed and purified by distillation. Concepts/ techniques studied: control of
the addition of a liquid during an exothermic reaction, liquid-liquid extractions, distillation under atmospheric
pressure, analyses of the boiling point (correction of emerging column), refractive index, infra-red spectrum of
a liquid, NMR 1H, 13C and DEPT135 (theoretical).
Experiment 3: Iodination of Vanillin (100 points-Business Memo report)
4-Hydroxy-3-methoxybenzaldehyde (vanillin) is reacted with iodine, generated in situ from sodium iodide and
bleach, to produce an iodinated aromatic compound. Concepts/ techniques studied: Aromatic electrophilic
substitution, 1H NMR, MP, IR analysis.
Experiment 4: Dehydration of 2-methylcyclohexanol (100 points-Business Memo report)
This experiment involves reaction of phosphoric acid with 2-methylcyclohexanol to produce alkenes which will
be analyzed gas chromatographic analysis. Techniques studied: 1H NMR, IR analysis, GC analysis.
Experiment 5: Grignard reagent synthesis and reactivity (200 points-Full lab report)
Bromoanisole is reacted with magnesium to form a Grignard reagent (in situ). Two equivalents of the formed
Grignard reagent is then reacted with p-N,N-dimethyl benzoate to form the corresponding alcohol (“leuco”)
product. The leuco product is dehydrated to synthesize a highly conjugated colored dye (similar to malachite
green or crystal violet). Concepts/ techniques studied: Organometallic reagents, anhydrous solvents, NMR, IR
analysis.
Experiment 6&7: Bromination of butylcinnamate (200 points-Full lab report)
The butyl cinnamate is brominated by in situ generated bromine. The reaction is monitored by thin layer
chromatography (TLC). The product is extracted, the organic layer is washed, dried and evaporated. The
conversion is estimated by NMR analysis of the crude product. TLC study will allow student to find the most
efficient eluant for flash chromatography for purification. Concepts/ techniques studied: TLC eluant study, flash
chromatography, conversion and stereoselectivity of the reaction will be studied using NMR spectra, MS.
Reports are typically due 1 week after completing the experiment (be sure to reference the deadline on the
assignment). Some reports will take the form of a business memorandum which specifically addresses the
questions raised in the letter at the beginning of the experiment package. These memos are very short, and
will be graded for accuracy, completeness, and style. Be sure to include table of data and spectra as
attachments.
For two experiments, the reports take the form of detailed technical reports rather than the business
memoranda. Laboratory reports are to represent the work of each individual, except where otherwise stated.
The reports should reflect each individual student's procedures, results, interpretations, conclusions, etc. For
those aspects of a report which involve group data, each student is required to provide his/her own procedure,
interpretations, conclusions, etc.
Recommendations:
1. Read the entire laboratory package and assignments in the Techniques Manual. Attend the lectures.
2. Complete prelab assignments. This will help you focus on the laboratory procedure.
3. Write a thorough set of instructions in you laboratory notebook prior to the laboratory period, consulting the
model lab pages on the web. The procedure in your lab notebook can be used during the pre-lab quiz.
4. Pay attention to prelaboratory demonstrations.
Prelab Quiz (60 points)
At the beginning of each laboratory period there will be a short prelab quiz which covers the experiment that
you are about to perform. You will have access to your notebook during this quiz. The quiz will examine your
understanding of the procedure, and facts which should appear in your notebook if you are to be able to
successfully complete the laboratory.
One-page essay/wall posts (40 points)
Students are required to submit a weekly face book wall post to document their experience in the program. A
1-page reflective essay by each student on his/her experience in the class is due at the final exam. The
student should draw upon knowledge/concepts learned as part of coursework and field trips.
Lab notebook, safety, technique (100 points)
Student will be assessed on the completeness of his/her lab notebook (e.g. reaction schemes, dates, recorded
observations, data. tables etc). The instructor (with input from TAs) will assign a safety/lab techniques grade
related to the student’s work performance in the lab.
Lab Practicum and final exam (200 points)
The lab practicum will involve a condensation, recrystallization, and determination of melting point similar to
Experiment 1. You will have 1hr 45 min to perform the experiment. You will also complete a paper-based final
exam covering topics introduced in the lab (allotted time 1hr 15min).
GEORGIA TECH HONOR CODE
All students are expected to abide by the Georgia Tech Honor Code (www.honor.gatech.edu)