Chemistry 226 - Organic Chemistry Laboratory I
Fall 2007
Instructor: Dr. Jeremy Wessel
Office: Bea 206
Office Phone: (985) 448-4504
E-mail: phsc-jjw@nicholls.edu
Office Hours: 9:40-11:40 MWF, 1:00-4:00 T, 10:30-11:30 R, 1:00-3:00 F
Catalog Description: Chemistry 226. Organic Chemistry Laboratory I. 2-0-6. Prerequisite: CHEM
110. Prerequisite or corequisite: CHEM 222. An introduction to the study of the properties and
preparation of organic compounds. (40.0504)
Prerequisite: CHEM 110
Prerequisite or corequisite: CHEM 222
Required Texts and Other Materials:
1 – Lab Manual, Chemical Education Resources
2 - Safety goggles
3 - Laboratory notebook. Bound, duplicating with tear out sheets
Required Supplemental Readings: None
Course Goals: The student will develop an understanding of and employ proper techniques used
in organic synthesis, data collection, product analysis, and documentation.
Student Outcome Objectives:
At the end of this course the student will be able to
 Separate different compounds based on solubility,
 Extract products from various solvents,
 Recrystallize products,
 Perform fractional and simple distillation,
 Synthesize various organic compounds,
 Analyze and identify organic compounds by infrared spectroscopy, thin-layer
chromatography, gas chromatography, and nuclear magnet resonance.
Course Content: (see schedule for order)
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Melting Points
Recrystallization
Distillation
Extraction
Thin-Layer Chromatography
Gas Chromatography
Infrared Spectroscopy
NMR Spectroscopy
Isolating Caffeine from Tea
Dehydration
Esterification
Nucleophilic Substitution
Electrophilic Aromatic Substitution
Reduction
Synthesis of Phenacetin
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The Aldol Condensation
Course Requirements:
All students will perform experiments using proper safety practices.
Notebook: 25 points/experiment
13 experiments
325 points
Aldol experiment formal report
50 points
Midterm Exam
100 points
Final Exam
100 points
575 points
Method of Evaluation: Grades will be determined using the following scale:
A: 90-100
B: 80-90
C: 70-80
D: 60-70
F: <60
Make-up Policy: Missed labs can be made up for an excused absence. Make-ups must be
completed within two weeks of the experiment date.
Attendance Policy: Attendance is mandatory.
Academic Honesty Policy: Anyone found cheating will be subject to the penalties stated in
Student Code of Conduct including but not limited to a score of zero on exam, expulsion from the
class or expulsion from the University.
Semester Withdrawals: The last day to withdraw from the class with a ‘W’ is October 26, 2007.
Academic Disabilities Policy: If you have a documented disability that requires assistance, you
will need to register with the Office of Disability Services for coordination of your academic
accommodations. The Office of Disability Services is located in Peltier Hall, Room 100-A. The
phone number is (985) 448-4430 (TDD 449-7002).
Class Disruptions: The use of cellular phones, pagers or any other electronic personal device is
prohibited in class. Any infractions will result in dismissal from class and 0 for the experiment.
Academic Grievances:
The proper procedure for filing grade appeals or grievances related to academic matters is listed
in Section 5 of the Code of Student Conduct and at the following link:
http://www.nicholls.edu/documents/student_life/code_of_conduct.pdf.
Continued Learning following an Extreme Emergency:
In order to make continued learning possible following an extreme emergency, students are
responsible for:
•
reading regular emergency notifications on the NSU website;
•
knowing how to use and access Blackboard (or university designated electronic delivery
system);
•
being familiar with emergency guidelines;
•
evacuating textbooks and other course materials;
•
knowing their Blackboard (or designated system) student login and password;
•
contacting faculty regarding their intentions for completing the course.
Faculty are responsible for:
•
their development in the use of the Blackboard (or designated) software;
•
having a plan for continuing their courses using only Blackboard and email;
•
continuing their course in whatever way suits the completion of the course best, and
being creative in the continuation of these courses;
•
making adjustments or compensations to a student’s progress in special programs with
labs, clinical sequences or the like only in the immediate semester following the emergency.
NOTEBOOK
Prelab
ANSWERS TO PRELAB QUESTIONS from manual
In Notebook:
 TITLE and DATE
 PURPOSE: Describe what is expected of the laboratory. This should be only one or two
sentences, in your own words--do not copy from the manuals.
 DATA TABLE: Listing of all of the reagents and solvents used in the experiment as well as the
products. List in table form only. Include all data you need for the experiment or report.
(You’ll need to develop judgment to decide relevance.) Also copies of reference spectra when
appropriate. Note potential hazards. Chemfinder (http://chemfinder.cambridgesoft.com/) is a
good reference, as are the CRC Handbook, Merck Index, and Aldrich catalog (available
outside my office).
 CHEMICAL EQUATIONS (IF ANY): Write all of the major chemical reactions and side reactions
for the experiment. Include the amounts called for in the experiment, determine which is the
limiting reagent and determine the theoretical yield.
In lab
 PROCEDURE/OBSERVATIONS – write down what you do and what happens as you do it
Report spectral data in table form:
for NMR
Chemical Shift (ppm)
Integration
Multiplicity
for IR
Wavenumber
Description
Functional Grp
Postlab
 CALCULATIONS: Show all your work. Must be legible and organized.
 CONCLUSION: Report final results (positive or negative) and what evidence was used to make
conclusions. (Compare with PURPOSE.)
 ANSWERS TO POSTLAB QUESTIONS
 DISCUSSION: Discuss any results not covered already in the postlab questions
 REFERENCES: Proper citation of all material used in writing the report or to gather
background material.
Journal Citation: authors (last name, first name), title of journal, year of
publication volume, page number
Example: Smith, R. A.; Jones, M. J. J. Am. Chem. Soc. 1965, 80, 295.
Notebooks must be written legibly to avoid loss of points.
Schedule of Experiments
Day
20 August
Experiment
Check In/Safety
Day
22 August
27 August
3 September
10 September
17 September
TECH 703 Recrystallization
Labor Day Holiday
TECH 705 Extraction
TECH 707/TECH 709
TLC/GC
Review
SYNT 732 Isolating Caffeine
SYNT 713 Esterification
29 August
5 September
12 September
19 September
17 October
22 October
29 October
5 November
12 November
REAC 714 SN1 & SN2
Reactions
REAC 716 Nitration
REAC 715 Reduction
SYNT 726 Phenacetin
SYNT 720 Aldol Condensation
19 November
26 November
Thanksgiving Vacation
Review/Check Out
21 November
28 November
24 September
1 October
8 October
15 October
26 September
3 October
10 October
24 October
31 October
7 November
14 November
Experiment
TECH 701 Melting
Points
TECH 704 Distillation
TECH 704 Distillation
TECH 705 Extraction
TECH 710/TECH 711
IR/NMR
Midterm
REAC 712 Dehydration
SYNT 713
Esterification
REAC 714 SN1 & SN2
Reactions
REAC 716 Nitration
REAC 715 Reduction
SYNT 726 Phenacetin
SYNT 720 Aldol
Condensation
Thanksgiving Vacation
Lab Final