CHEM 2212 – Organic Chemistry Laboratory II
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I.COURSETITLE:Organic Chemistry II Laboratory
COURSENUMBER: 2212CATALOGPREFIX: CHEM
II.PREREQUISITES: CHEM 2201 & 2211
COREQUISITE: CHEM 2202
III.CREDITHOURS:1LECTUREHOURS: 0
LABORATORYHOURS: 1(3 contact hrs.)OBSERVATIONHOURS: 0
IV.COURSEDESCRIPTION:
A course designed to give the student hands-on laboratory experience with the concepts of Organic Chemistry 2202 and the use of experimental apparatuses and techniques in the practice of organic chemistry. Emphasis will be on microscale technique due to its safety and economy of time and resources as well as its frequent need in biochemical, natural product, environmental and pharmaceutical fields; however, some macroscale experiments may be performed. Experiments will generally cover experimentally the concepts studied in Organic Chemistry 2202 including Friedel-Crafts, nitration, and other electrophilic substitution reactions of the aromatic ring; oxidation of alcohols; epoxidation of alkenes; preparation and reaction of organometallic compounds; the aldol condensation; and infrared and un/visible spectrophotometry formation and reaction of carboxylic acids and their derivatives; amines; phenols; versatile synthetic techniques such as theacetoacetic ester and malonic ester syntheses and aromatic diazonium saltreactions; carbohydrates; lipids; and proteins and other polymers.
V.ADOPTEDTEXT (S):
Macroscale and Microscale Organic Experiment
7th Edition
by: Kenneth L. Williamson
Cengage, 2016
ISBN: 978-1-305-57719-0
VI.COURSEOBJECTIVES:
At the end of the course, the student should be able to:
1.Visualize the interconversions among various classes of compounds such as alcohols, aldehydes and ketones via oxidation and reduction, and have a general idea of the reagents and conditions to effect these interconversions
2.Understand the basic concepts of and the actual experimental procedures out electrophilic aromatic substitutions of aromatic compounds, including Friedel-Crafts alkylations and acylations, nitrations, and halogenations
3.Understand nucleophilic addition to the carbonyl group and how it is used synthetically in the aldol condensation and other reactions
4.Understand and perform conversions of carboxylic acids and their derivatives into more stable derivatives of those compounds
5.Synthesize a variety of esters by several techniques, including the Fischer esterification
6.Understand the basic concepts of and the actual experimental procedures to carry out a malonic ester or acetoacetic ester synthesis and the further reactions possible to form various acids and substituted barbiturates
7.Conduct a Grignard synthesis of an alcohol
8.Understand and use the various types of aldol and Claisen condensations
9.Use chemical properties to separate ingredients of a complex mixture
10.Test for different types of carbohydrates and understand the chemistry of the tests
11.Perform catalytic hydrogenation of an unsaturated vegetable oil and hydrolyze it to its constituent fatty acids
12.Differentiate between monomers and polymers, including amino acids and proteins, and understand how they are related experimentally
CHEM 2212 – Organic Chemistry Laboratory II
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VII.GRADING:
A = 90 – 100
B = 80 – 89
C = 70 – 79
D = 60 – 69
F = 0 – 59
VIII.COURSEMETHODOLOGY:
Laboratory space with fume hoods and other needed supplies such as chemicals, gas, cold water, ice, and instrumentation. Required personal protective equipment other than safety goggles. Computer with projector to display the contents of the CD-ROM that accompanies the text for illustration of techniques and experiments and the molecular modeling CD-ROM from the Carey text used in CHEM 1201-1202. Molecular models for additional hands-on demonstration of the structure of organic chemicals.
IX.COURSE OUTLINE:
1.Laboratory safety and proper care of instrumentation
2.Electrophilic aromatic substitution reactions
A.Fiedel-Crafts alkylation and acylation
B.nitration and halogenation
4.Oxidation and reduction reactions
A.alcohols to aldehydes and ketones and vice versa
B.epoxidation reactions
5.Preparation and reactions of ferrocene
6.The aldol condensation
7.Chemiluminescence of luminol
8.Molecular modeling of compounds
A.carboxylic acids and their derivatives
B.amines
C.phenols and aryl halides
D.basic biomolecules like carbohydrates, lipids and proteins
9.Conversions of carboxylic acid derivatives into more stable derivatives
A.esterifications starting from acids and from acid anhydrides
B.formation of amides
10.The malonic ester and acetoacetic ester syntheses
11.Preparation and reactions of a Grignard reagent
12.Separation of a complex mixture based on chemical properties
13.Condensation reactions
14.Carbohydrate identification
15.Catalytic hydrogenation of olive oil and hydrolysis
16.Polymers
LABORATORY SCHEDULE
Week # / Description1 / Introduction to Laboratory, Laboratory Safety
Experiment 1: Friedel-Crafts alkylation
2 / Experiment 2: Grignard synthesis and reaction
3 / Experiment 3: Fisher esterification
4 / Experiment 4: Determination of syn vs anti addition
5 / Experiment 5: Synthesis of ethanol by fermentation
6 / Experiment 6: Friedel-Crafts acylation
7 / Experiment 7: Wittig reaction
8 / Experiment 8: Aldol condensation
9 / Experiment 9: Preparation of an azo dye
10 / Experiment 10: Synthesis of a carboxylic acid
11 / Experiment 11: Fatty acid composition of vegetable oil and saponification
12 / Experiment 12: DNA extraction, making cheese, and the use of lecithin to make mayonnaise
13 / Experiment 13: Carbohydrate characterization
14 / Experiment 14: Synthesis and spectral analysis of aspirin
15 / Lab Final and Checkout
16 / Final
X.OTHERREQUIREDBOOKSANDMATERIALS:
Safety goggles (laboratory fume hoods, aprons, gloves, and any other necessary
personal protective equipment will be supplied). Laboratory equipment and
chemicals will be supplied in the class.
XI.EVALUATION:
Student evaluation is by quizzes and laboratory worksheets which may include experimental data to be recorded, results to be calculated, and application questions to be answered or discussed in class.
XII.SPECIFICMANAGEMENTREQUIREMENTS:
Students who exhibit behavior that is disruptive to the learning process will after a verbal warning be dismissed from the class.
In the laboratory, students are required to follow all safety rules and procedures specified by the instructor. Anyone not working quietly and safely will be asked to leave and will receive a zero for that day's lab assignment.
XIII.OTHER INFORMATION:
FERPA: Students need to understand that your work may be seen by others. Others may see your work when being distributed, during group project work, or if it is chosen for demonstration purposes.
Students also need to know that there is a strong possibility that your work may be submitted to other entities for the purpose of plagiarism checks.
DISABILITIES: Students with disabilities may contact the Disabilities Service Office, Central Campus, at 800-628-7722 or 937-393-3431.