The City College of New York - Department of Chemistry
Chemistry 26200; Organic Chemistry Laboratory, Section 4PS
Fall 2009
Instructor: Prof. Urs Jans, 212-650-8369, email: ujans@ccny.cuny.edu
Office location: MR-1218, Office Hours: W: 3-4 pm, Th: 11-12 am, or by appointment
Teaching Assistant: Faiza Anwar, email: fanwar118@gmail.com, MR-1106
This course is stressing the techniques involved in the preparation, isolation, purification and analysis
of carbon compounds (for non-chemistry majors).
The pre-requisites for this course are Chem 10401 and Chem 26100.
Room: MR-1109 (recitation), MR-1109 (lab)
Class time: Thursday: 2:00 – 2:50 pm (recitation) and Thursday 3:00 – 5:50 pm (lab)
Textbook: Signature Laboratory Series – Organic Chemistry Laboratory 26200 (available from the
Bookstore)
Grading Policy
Midterm exam
Cumulative lab exam
Laboratory reports (12 out of 13)
Quizzes (5 out of 6)
Lab participation
15 %
25 %
40 %
15 %
5%
* Missing a lab will result in receiving a zero grade for that particular lab and thus dropping that grade. No make-up
labs or exams are given, except if you are absent for verifiable medical reasons.
Grade Assignment
A+ 97-100
A 93-96
A- 90-92
B+ 87-89
B 83-86
B- 80-82
C+ 77-79
C 73-76
C- 70-72
D 60-69
F 0-59
Quizzes: There will be 6 unannounced quizzes at the beginning of the recitation.
The Laboratory Examination: The laboratory examination will test the student’s knowledge of the
theoretical basis of the experiment he/she has performed. It will include all of the recommended
reading, the theory of the reactions performed, and of the techniques applied.
The Laboratory Report: Laboratory for each experiment must be handed in no later than one week
after completion of that experiment.
A laboratory report for an experiment addressing a laboratory technique (TECH) has to address all
the points at the end of the description of the experiment.
You must prepare your laboratory reports for the synthesis experiments (REAC or SYNT) in
accordance with the following outline.
1
2
3
4
5
6
7
8
9
Name, ID number and section
Title of experiment
Aim of experiment
Any equations chemical structures relevant to the experiment as well as any
pertinent mechanisms.
A table listing the compounds used, their molecular weights, amounts used in
grams and moles, boiling points and density (for liquids), as applicable
Hazards: determine flammability, toxicity or corrosiveness of the compounds
used in this experiment
Procedure and Observations: Describe exactly how you performed the
experiment and exactly what observations were made (e.g., color change, if
any spillage occurred etc.). The observations have to be very specific. Draw a
separation scheme or a flowchart. Always write this part in the third person and
in past tense.
Results: This part should include identification of the limiting reagent and
calculation of the theoretical yield of the product. Actual yield of the product,
physical properties of the compounds such as color or nature of product (e.g.,
colorless needles of compound X were obtained). Melting or boiling points.
Conclusions: Did you achieve what had to be achieved? Did you have any
problems, if so discuss these. Other scientific comments on the experiments,
such as suggestions if you feel you could do something differently to improve
the outcome of the experiment.
5
5
10
10
10
10
20
20
10
Information about reagent and chemicals can be obtained from a number of sources. The most
common resources are the CRC Handbook of Chemistry and Physics, the Material Safety Data Sheet
or the Aldrich Catalog. There are also a number of sources for this information online. A page listing
theses sources has been assembled by the campus science librarian at the url:
http://resources.ccny.cuny.edu/resources/subject.jsp?sub_id=62#273
Sections 1 to 6 are the components of the preliminary laboratory report. This part helps the student to
prepare for the proper performance of the relevant laboratory preparations and ensures the instructor
that all of the required reading has been done. Sections 1 to 6 have to be prepared at home, during
the week preceding the first laboratory session for the new experiment. The preliminary laboratory
report has to be ready at the beginning of the lecture of the laboratory session for that experiment.
Section 7, 8 and 9 must be completed in the laboratory. The sample lab report (hand out) might also
give you some insight in how the different sections are structured.
The completed laboratory report is handed in on the last day assigned for the particular experiment.
Handing in the lab report after this deadline results in a deduction of 20 points from the mark of this
lab report.
Schedule: The schedule shows the experiments that will be performed and when the exams will be
held. The chapters, which describe techniques especially relevant to each experiment are listed in
italics adjacent to the experiment numbers. You are strongly advised to read these chapters in the
textbook. Since some techniques will be used more than once in the laboratory course, the
examination questions on techniques will be chosen based only on the relevance of the techniques to
the particular laboratory experiment.
Make-up Sessions, Absences: No make-up exams, or laboratory sessions, can be arranged. It is
the student’s responsibility to ensure that he/she can attend all the laboratory sessions, on time. An
absence from a laboratory without a suitable strong excuse will result in a mark of zero being
assigned.
Cumulative Laboratory Exam: A cumulative laboratory exam (90 min) will be given at the end of the
course (Dec. 10) and accounts for 25% to the final mark of the course. The cumulative laboratory
exam will focus on the techniques and not on the reaction mechanisms.
Safety: All of the safety regulations must be adhered to. (Safety goggles will be worn at all times.
Sandals are not allowed in the lab). Any willful violation of our safety rules will result in the student’s
immediate expulsion from the laboratory and a course grade of F.
Breakages: Students must be aware of the fact that they will be charged the replacement cost of
any equipment, which they break during the lab course. Some of our glassware is especially
expensive and so you are urged to work carefully at all times.
Academic Integrity: The CCNY policy on academic integrity will be followed. A document is posted
on the CCNY website (CUNY policy on academic integrity:
www1.ccny.cuny.edu/facultystaff/provost/upload/academicintegrity.pdf-2007-01-19). Make sure you
have read the details regarding plagiarism and cheating, in case you are not clear about the rules of
the college. Cases where academic integrity is compromised will be prosecuted according to these
rules.
Course Learning Outcomes for Chem 26200:
1. To understand the physical principles underlying the techniques used for purification of
compounds, separation of reaction mixtures, monitoring reactions and analyzing reaction
products in organic chemistry lab.
2. Understand the mechanistic basis of synthetic experiments.
3. To learn and execute several fundamental organic laboratory techniques used.
4. To perform fundamental organic reactions.
5. To learn the safety precautions required in an organic lab.
6. To learn the calculations associated with synthetic organic experiments.
7. To learn how to make observations, collect data and write a lab report for an organic synthesis
experiment.
City College of New York – Chemistry Department
Chemistry 26200 – Organic Chemistry Laboratory – Fall 2009, Section 4PS
Schedule of Experiments:
Sept. 3
Introduction, Check In, Melting Points of Compounds and Mixtures
TECH 701
Sept. 10
Purifying Acetanilide by Recrystallization
TECH 703
Sept. 17
Separating Cyclohexane and Toluene by Distillation
TECH 704
Sept. 24
Separating Acids and Neutral Compounds by Solvent Extraction
TECH 705
Oct. 1
Separating Ferrocene and Acetylferrocene by Adsorption Column
Chromatography
TECH 708
Oct. 8
Gas Chromatography and Thin Layer Chromatography
Oct. 15
Brominating Alkenes (Group 1); Identifying an Unknown Compound
by Infrared Spectroscopy (Group 2)
TECH 719
TECH 710
Oct. 22
Brominating Alkenes (Group 2); Identifying an Unknown Compound
by Infrared Spectroscopy (Group 1)
TECH 719
TECH 710
Oct. 29
Qualitative Test for Alkenes and Identifying an Unknown Compound
by Infrared Spectroscopy
TECH 472
Nov. 5
Studying SN1 and SN2 Reactions: Nucleophilic Substitution at
Saturated Carbon
REAC 714
Nov. 12
Dehydrating Cyclohexanol
REAC 712
Nov. 19
Nitrating Methyl Benzoate
REAC 716
Dec. 3
The Aldol Condensation: Synthesis of Dibenzylacetone
SYNT 720
Dec. 10
Equipment Check Out