MANHATTAN COLLEGE DEPARTMENT OF CHEMISTRY & BIOCHEMISTRY
ORGANIC CHEMISTRY LABORATORY CHEM 324
Spring 2013 SYLLABUS
Raymond Chung, PhD
Office: Hayden 402
Phones: (718)-862-7211
Office Hours: TBA
Laboratory: Hayden 503
Prelab:
Hayden 201
Time: Tuesday, Sec. 4, 1:25-5:25 PM
Requirements:
1. Students must have successfully completed or be taking Chem 320
concurrently.
2. Students must checkout properly on the specified date or before withdrawing
from the course.
3. Students must follow all Safety Regulations while working in the laboratory.
4. Students must obtain their own safety goggles and wear them at all times in
the lab.
5. Students must attend pre-lab lectures. Students failing to come to pre-lab will
be asked to leave and will be given a zero for the experiment.
6. Students must come prepared to the lab with a written outline of the
experimental procedure (prelab.) in the lab notebook. Students who do not
come prepared will be asked to leave and will be given zero for that
experiment. Coming unprepared is a safety hazard.
7. Students must attend the lab session that they are registered for. Exceptions
will only be made in severe (documented) cases.
Required Material: Experimental Organic Chemistry, Daniel R. Palleros, John-Wiley, 2000. A
ruler, calculator and safety glasses.
Course Goals:
Purification/Isolation/Synthesis Methods and Criteria of Purity
To learn the basic skills required to work in an organic chemistry laboratory, e.g.,
Reaction setup, chemical isolation & purification, analysis of purity of organic
compounds and methods for characterization of compounds by chemical and
spectroscopic methods.
Course Schedule:
(Experiment 1)(Week 1 & 2) Spectroscopy- Identification of unknown organic
compounds using infrared (IR) and nuclear magnetic resonance (NMR) spectroscopy.
See handout for experimental procedure. (Full Lab Report)
(Experiment 2) (Week 2 & 3) Electrophilic Aromatic Substitution– Synthesis of 4-(phydroxyphenyl)-2-butanone (Raspberry Ketone) via Friedel-Crafts Alkylation of phenol
with 4-hydroxy-2-butanone. See handout for experimental procedure. (question
sheet)
(Experiment 3) (Week 4) Grignard Reaction – Synthesis of Malachite Green or Crystal
Violet ( triarylmethane dyes) using a Grignard reaction. See handout for experimental
procedure. (question sheet)
(Experiment 4) (Week 5) Oxidation and Reduction– oxidation of p-toluic acid to
terephthalic acid. Reduction of Camphor (a chiral ketone) into borneol and isoborneol using sodium borohydride as a reducing reagent. Experiment E21.2 and E21.7
Read Palleros pgs 438-472.(question sheet)
(Experiment 5) (Week 6) Ether Synthesis – Synthesis of 2-methoxynapthelene from
methanol and 2-napthol using an acid catalyzed condensation reaction. See
handout for experimental procedure.(question sheet)
(Experiment 6) (Week 7) Wittig Type Reaction – Preparation of ethyl cinnamate (a
fragrance compound found in cinnamon and certain fruit) from benzaldehyde via the
use of a stabilized Wittig reagent. See Handout for experimental procedure.(Full Lab
Report)
(Experiment 7) (Week 8) Esters Formation and Hydrolysis - Preparation of propyl
acetate and isoamyl acetate by Fisher esterification . In addition the hydrolysis of the
esters in fat (saponification) will be examined. Experiment 22A.2 Palleros 480-485. Also
see handout for saponification. (question sheet)
(Experiment 8) (Week 9&10) Aldol Reaction and UV-Visible Spectroscopy . - Synthesis
of -ionone and/or -ionone (compounds used in the fragrance industry) by the use
of an aldol reaction. Experiment 23B Palleros 520-531.(Full Lab Report)
(Experiment 9) (Week 11 & 12) Multi-step Synthesis – Synthesis of Lidocaine. The local
anesthetic lidocaine (xylocaine®) is synthesize in a 3 step procedure starting from 2,6 –
dimethyl-nitrobenzene. The first step involves the reduction of the nitro compound into
the corresponding amine. The second step involves amide formation by reacting the
amine with an acid chloride. Finally the amine group is introduced in the final step via
an Sn2 reaction. See handout for experimental procedure.(Full Lab Report)
(Experiment 10) (Week 13)
Formation of Azo dyes – a variety of azo dyes will be formed by reacting aromatic
diazonium salts with activated aromatic rings (via an electrophilic aromatic substitution
reaction). Experiment 27.1 (orange II) & 27.3 Read pages 612-615 and 630-631 in
Palleros See Handout for additional information.(question sheet)
Final Exam May 9-15 –NOTE: organic lab has a common final which can be scheduled
any where during finals week. Do not schedule travel plans during finals week.
Grading & Evaluation:
A students grade is determined by a combination of their laboratory technique,
laboratory reports and tests. Each different criteria is given the following weight.
Technique
Laboratory Reports
Midterm (10 %) and Final Exam (15%)
35%
40%
25%
(a) Technique - The technique score is effected by the following: prelab notebook, following
proper laboratory safety procedures, lab experiment results, glassware breakage,
cleanliness, turning off and returning equipment etc.. A bound composition notebook must
be used as the laboratory notebook. This notebook is to contain all necessary pre-lab
material as well as a record of all the observations and data collected in the lab in a well
organized fashion.
(b) Laboratory Reports – A formal report is required for every experiment. The reports must
follow the format specified in class. All Laboratory reports must be typed on a word
processor (including tables). All chemical structures however may be drawn in by hand.
Each laboratory report is due on the dates listed above. Laboratory reports must be handed
in on time. Reports that are late suffer a penalty of 5% a day. If a report is not submitted by
the time the reports are returned to the class the student receives a zero for the experiment.
Most lab reports are graded on the basis of ten points except for a few of the longer
Reports must be
handed in during class or in my mailbox. DO NOT Slide them under
office doors, email them, leave them in the baskets in the hallway or
leave them in other locations.
multistep experiments which are graded out of 15 or 20 points.
(c) Exams - There are two exams in this class, a midterm and final. The date of the midterm
is listed in the syllabus and lab calendar. The final is a common exam. Common exams can
be scheduled any where during finals week. Do not schedule travel plans during finals
week. There are NO make-up exams given under any circumstances.
The grades are determined by using the distribution of students overall combined grades. In
general, the median grade will be a “C to C+” grade. An “A” grade is given only for
distinctive and outstanding achievement. A”B” grade is an above average grade.
Attendance:
Absence from lab will result in the student getting a zero for that experiment (In both
report and technique scores). Missing a test will result in a grade of zero for that test.
Exceptions will only be made in severe (documented) cases.
College Policies – (1) All written work must conform to standard English usage. Failure to
meet such standards will affect your grade. (2) The college subscribes to the principle of
academic integrity. Incidents of cheating, facilitation of dishonesty or plagiarism may result in
a “F” grade for the course. Copying sections of a lab report from other students is
not acceptable. If this occurs all students involved will be penalized. The penalty will be
dependent on the severity of the offense.
Copying sections of a text book or web
site directly into your lab report is also not acceptable. We already know the text
book author understands the experiment; the goal of writing the report is to show that you
understand it. As with copying from other students this will incur a penalty to your lab grade
which depends on the severity of the offense.