CCBC Catonsville

Division of Math & Science

CHEM 203 Organic Chemistry II Laboratory is the second semester of a two-semester laboratory sequence in organic chemistry. The techniques of synthesizing , isolating and identifying organic compounds will be emphasized. Students will identify a series of unknowns using both classical qualitative and spectroscopic techniques. Students will be encouraged to work on an independent project involving a multi-step synthesis. Successful completion of CHEM 200 and 201 (or its equivalents) are the prerequisites for the course.

Semester: Spring 2006

Course Meeting and times:
CHEM 203 LbB Wed: 2:30-5:25 PM
CHEM 203 LbC Wed: 7:05-10:00 PM

Instructors: A section Dr. Yau, C section Dr. George Farrant

Office Location and Telephone:

Course Description: This course is designed to satisfy the needs of students who are in curricula that requires completion of a full year of organic chemistry.

Instructional Methods and Materials: Text:

1. Laboratory Manual CHEM203 By Drs. Ji Hyun Kim and Crystal Yau & George Farrant available in book store
2. A bound Laboratory Notebook:The pages must be sewed (not loose leaf) and the pages numbered. Leave two pages at the beginning for a table of contents.
3. Laboratory apron and and set of goggles

Instructional Methods and Materials:
Students enrolled in CHEM 203 are expected to maintain a laboratory notebook that accurately documents their work. Entries in the notebook must be made as work is being carried out. After an experiment is completed students will write a laboratory report about the experiment. The lab report should be word processed and include the following: 1. Title , 2. date work was performed, 3. name of the student writing the report and names of students involved in the project. 4. Purpose, 5. A balanced equation showing the structures of the reactants and the products 6. Procedures used (this can be in a numbered format or in paragraph form). 7. Results and discussion. (In this part students must include all spectroscopic data and an interpretation of the relevant peaks which allows one to assign a structure) If a gas chromatograph was used, the conditions of the analysis must be included (type of column used, temperature, Helium gas flow rate and compound assignments for the peaks (if possible). Then there must be a succinct conclusion which must reflect the purpose of the experiment. (e.g.: desired product was obtained in ____% yield and ___&purity). The Laboratoy notebook will be checked perioicialy thoughout the semester the semester and will count as 10 pts

Grading Policy:
Grades awarded to students enrolled in CHEM 203 will be computed by totaling the points earned on the experiments and dividing the total by 130 and multiplying by 100% to convert to a percentile score.

Attendance Policy: Students are expected to perform all the experiments. If a student is absent from the assigned lab period he/she may make up the experiment on a later date. The makeup work must be coordinated with both the instructor and the laboratory manager. If you miss a lab it should be made up by the next week.

Laboratory Schedule
Experiments & Title References

Week Date	Title	Reference	Points
1: Feb. 1	Check in and Fermentation of Sucrose. Prepare a fermentation vessel and charge with 50 ml of water and 35 gms of sucrose. Add yeast + nutrients and allow to ferment with CO 2 trap at 30 degrees Celsius until next week.
2: Feb. 8	Preparation of Ethanol: Distill your ethanol mixture (simple) and collect 20 ml. Dilute the distillate with water to 50.0 ml and determine % composition via refractive index. Turn in a labeled vial containing a sample of your product with your word processed report Answer questions 1,2&3 page 8		10
3: Feb. 15	Oxidation of Cyclohexanol to Cyclohexanone Follow the directions in Experiment 2 using 0,075 mols of alcohol. Isolate your product determine % yield, Take the ir spectrum and refractive index. Compare the properties of your product to those reported in the literature. Turn in the product with your word processed report. Answer questions 1-4 pg 11		10
4: Feb. 22	Grignard Project: Do the Prelab before coming to class. Working with a partner, submit a plan for your Grignard Project; Select the appropriate alkyl halide and ketone you will use from the list in the lab book.. Look up the properties of the product you expect to form. After an OK from you instructor, prepare the alcohol from the ketone and alkyl halide which you chose plan to make approximately -0.20 mol of product.
5: Mar. 01	Work up of Grignard product. Isolate and purify the alcohol you prepared. Determine its properties, % yield, and ir spectrum and compare them to values reported in the literature. Submit your product in a labeled vial when you turn in your word-processed report. Answer the questions: 1-3 pg 14		20
6: Mar. 08	Prepn of Aspirin Prepare a sample of aspirin using the macroscale procedure on pg 18 (1.0 gm of salicylic acid, 2 ml acetic anhydride and five drops of conc sulfuric acid). Test your product with FeCl 3 soln for possible unreacted salicylic acid. Determine % yield, take mp. Compare the properties of your product with those reported in the literature. Turn in sample with your word processed report. Answer questions 1 & 2 pg 22		10
7: Mar. 15	Preparation of N,N, Diethyl-3-methylbenzamide "OFF" Starting with 0.02 mols of 3 methylbenzoic acid prepare the acid chloride by reaction with thionyl chloride and then convert that product into the final amide by reaction with an excess of diethyl amine. Isolate the product, take its ir spectrum % yield and compare its properties to those reported in the literature. Turn in your product with your word-pressed report. Answer questions 1 & 2 pg 28		10
8: Mar. 22	Aldol Condensation Reaction Preparation of Dibenzylacetone Prepare 0.30 mol of this aldol product using the procedure on pg 20. Determine % yield, mp, take and interpret ir spectrum, Compare the properties of your product with those reported in the literature. Turn in product with your word-processed report. Answer questions 1-3 pg 21		10
9: Mar. 29	Nitration of methylbenzoate Prepare ~0.05 mols of methyl 3-nitrobenzoate by nitrating 0.050 mols of methyl benzoate. Recrystaillze the slightly yellow product from methanol, determine mp, % yield. Take and interpret the ir spectrum. Turn in sample with your word-processed report. Answer questions 1-5 pg 11		10
10: Apr. 05	Prepn of Orange II Prepare Orange II dye procedure on pg 22-24. Turn in your product with your word-process report. Answer questions 1-3 pg 26		10
	Spring Break April 10 through April 17, 2006		10
11: Apr. 19	Polymer lab: Prepare samples of nylon 6,6 from adipoyl chloride and hexamethylene diamine solutions (already prepared). Prepare polystyrene (PS) using procedure on pg 15-19. Turn in samples with your word-processed report. Answer questions: 1-3 pg 19		20
12-13 Apr.19 Apr. 26	Final Exam: Identification of unknowns (Identify one unknown and make a solid derivative of it) In your report explain how you arrived at the identification. Be sure to give both the structure of the unknown and the structure of the derivative. Turn in the sample of the derivative with your reports		20
	Turn in report for Expt 10 and the solid derivative. Check out of Lab & Check Out

Organic Chemistry II Laboratory

1. Care of Equipment At the beginning of the semester, each student will be assigned a locker which contains most of the equipment needed for carrying out subsequent experiments. Most of the equipment in this locker is expensive, and students are advised to be especially careful in the handling and storage of equipment. Students will be charged for damaged or missing equipment at the end of the semester.

2. Safety in the Laboratory Safety is of paramount importance in the organic chemistry laboratory. Students are expected to comply with the following rules in order to insure their safety and the safety of others. a) Safety glasses must be worn at all times. b) No open flames are to be used unless specifically directed by the instructor. c) Carefully follow instructions and heed all precautions. Ask your instructor if something is unclear. d) Avoid breathing chemical vapors. Use deck hoods and large fume hoods when working with volatile noxious chemicals. e) Avoid direct skin contact with chemicals. Wash affected area IMMEDIATELY with soap and water in the event of exposure. f) IMMEDIATELY notify your instructor in the event of an accident or injury. g) No food or drink allowed in the laboratory. h) Keep books and coats away from work area. i) No unauthorized experiments are to be conducted. j) Immediately wipe up spilled chemicals.

3. The Laboratory Notebook Each student will be expected to keep a laboratory notebook that will contain a complete, accurate, and up-to-date record of all completed laboratory work. 1. Number each page on the top right corner. 2. Leave the first 3 pages blank to serve as the table of contents. The table of contents should list the title of each experiment and the pages containing the write-up. A table of contents entry should be made as each new experiment is begun. 3. Each new experiment should begin with its title and the date on which work was initiated. 4. A brief statement of purpose. (Write this heading in notebook). In one or two sentences state what you are trying to accomplish in carrying out the procedure. 5. If you are carrying out a reaction to synthesize a new substance, you should show the balanced equation. 6. In a section titled, "List of Reagents" you should record the gram or volume amounts, molecular weights and mol amounts of chemicals used in the experiment. This should include solvents, drying agents and reactants. 7. In a section titled "Experimental Procedure" you should record what you did and what you observed. This record should be written in the past tense passive voice. Entries should be made while you are actually doing the work - not at some later time when your recollections may be hazy. Descriptions of procedures should include quantities used, color, temperature and time data where pertinent. Your description should be sufficiently detailed that a person having training in chemistry could repeat your work by following your write-up. Your write-up should also cite any references used in carrying out the procedure. 8. In a section titled "Results " you should summarize the results of the experiment. In a synthesis experiment you should cite the theoretical and percent yield (show calculations) and summarize physical measurements that confirm the identity and purity of your product. Be sure to compare the properties you found to those in the literature for the preparation of known compounds. Finally, there should be a conclusion. In this section you should describe the extent to which you achieved the objectives or purpose of the experiment. Please note that the notebook will be evaluated at the end of the course and is worth 10 pts.