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| CHEM134 syllabus
|COURSE NUMBER: ||CHEM134|
|COURSE TITLE:||Organic Chemistry II|
|IAI CODE(S):|| P1 904 P1 904L CHM 914|
|SEMESTER CREDIT HOURS:||5|
|STUDENT ENGAGEMENT HOURS:||225|
This course is the second of a two-semester sequence in Organic Chemistry for students pursuing chemistry, biochemistry, medical or engineering professions. Topics covered include nomenclature, molecular structure, reactivity and synthesis, with some extra emphasis on spectroscopy and applications to biological chemical reactions. Laboratory is required and offers more complex reactions than CHEM133 through the use of more sensitive reagents and multi-step reactions. Lecture meets three hours per week and lab meets four hours per week.
Completion of Organic Chemistry 1, CHEM133
(IAI: CHM913), the first semester of a year-long course, is required with a grade of a C or better.
A lab is required for this course. Some sections will require a separate lab, while other sections will include the lab.
STUDENT LEARNING OUTCOMES:
Students who complete this course should exhibit knowledge and competence in naming of organic compounds, their properties, formation and reactivity through chemical reactions and mechanisms. The student must be able to:
- Demonstrate knowledge of standard (International Union of Pure and Applied Chemistry, IUPAC) and
common nomenclature of organic compounds through the naming of chemical compounds. Classes of compounds
discussed in this course include, but are not limited to:
- Organometallic compounds
- Alcohols, diols and thiols
- Aldehydes and Ketones
- Carboxylic acids and their derivatives
- Enols and Enolates
- Carbohydrates, lipids, amino acids and nucleic acids
- Demonstrate comprehension of the properties and reactivity of organic functional groups by ranking
them in terms of bonding, nucleophilicity, electrophilicity, leaving groups, etc.
- Describe the methods and interpret spectra from basic analytical spectroscopic techniques such as gas
chromatography, mass spectrometry, IR spectroscopy, NMR spectroscopy and UV-Visible spectroscopy.
- Apply their knowledge of basic properties and reactivity of organic functional groups to drawing
reaction mechanisms which:
- Show proper flow of electrons.
- Predict products for the reaction of unfamiliar compounds.
- Distinguish between major and minor product formation.
- Apply their knowledge of chemical reactions and mechanisms to experiments in the laboratory by:
- Creating appropriate experimental setups with glassware and equipment.
- Synthesizing compounds in a time-efficient manner.
- Predicting the products of reactions by drawing the mechanism.
- Analyzing compound purity using spectroscopic techniques.
- Summarizing the results and analyzing experimental methods through writing.
- Spectroscopic Methods and Analysis (10%)
- NMR spectroscopy
- Background and uses
- 1H and 13C spectra interpretation
- 2D NMR
- Mass spectrometry
- Background and uses
- Spectral interpretation
- Infrared spectroscopy background and continued interpretation
- Organometallic Compounds (10%)
- Carbon-metal bonds
- Preparation of organolithium and organomagnesium compounds (Grignard reagents)
- Synthetic methods using organolithium and organomagnesium compounds
- Catalysis and metathesis
- Alcohols, Diols and Thiols (10%)
- Preparation of alcohols from aldehydes, ketones, carboxylic acids and epoxides
- Diol and thiol preparation
- Alcohol reactions and mechanisms-ether synthesis, esterification, oxidation and biological oxidation
- Ethers, Epoxides and Sulfides (10%)
- Nomenclature, structure and physical properties of ethers, epoxides and sulfides
- Preparation of ethers, epoxides and sulfides
- Reactions and mechanisms of ethers-Williamson ether synthesis and acid-catalyzed cleavage
- Reactions and mechanisms of epoxides-vicinal halohydrins to epoxides, nucleophilic ring opening and
acid-catalyzed ring opening
- Oxidation and alkylation reactions of sulfides
- Aldehydes and Ketones (10%)
- Nomenclature, structure and physical properties of aldehydes and ketones
- Preparation and sources of aldehydes and ketones
- Reactions and mechanisms of aldehydes and ketones
- Cyanohydrin formation
- Acetyl formation
- Primary and secondary amine reactions
- Wittig Reaction
- Stereoslectivity of reactions
- Carboxylic Acids and Carboxylic Acid Derivatives (10%)
- Nomenclature, structure and physical properties
- Acidity and acid strength and their effects on reactions
- Sources and preparation of carboxylic acids
- Carboxylation of Grignard reagents
- Hydrolysis of nitriles
- Nucleophilic acyl substitution and reactions of acyl chlorides to form other carboxylic acid
- Ester formation and reactions
- Enols and Enolates (10%)
- Nomenclature and regiochemistry
- Condensation reactions and mechanisms
- Aldol and mixed aldol condensation
- Claisen, mixed Claisen and Dieckmann cyclization
- Ester synthesis
- Effects of conjugation of alpha, beta-unsaturated aldehydes and ketones
- Conjugate addition, Michael and organocopper reactions
- Amines (5%)
- Nomenclature, structure and physical properties of amines
- Use of tetraalkylammonium salts for phase-transfer catalysis
- Preparation of amines through alkylation and reduction reactions
- Reductive amination
- Phenols (5%)
- Nomeclature, structure and physical properties of phenols
- Effects of substituents on phenol properties
- Naturally occurring phenols and uses of phenols
- Reactions of phenols-electrophilic aromatic substitution, Kolbe-Schmitt, and oxidation reactions
- Carbohydrates (5%)
- Classes of carbohydrates and nomenclature
- Structures of carbohydrates-Fischer projections and the D,L notation
- Reactions of carbohyrates-reduction and oxidation of monosaccharides, periodic acid oxidation,
synthesis of oligosaccharides
- Lipids (5%)
- Nomenclature, structure and physical properties of the classes lipids
- Biosynthesis of lipids and use of enzymes
- Amino Acids (5%)
- Classification and stereochemistry of amino acids
- Preparation of amino acids
- Biological reactions of amino acids
- Peptide synthesis and structures (secondary and tertiary)
- Nucleic Acids (5%)
- Structure and properties of pyrimidines and purines
- DNA structure and replication
- Ribonucleic acid structures, properties and biological roles
Weekly Lab Outline - Experiments completed in this semester use the techniques from CHEM133 to complete several "Name reactions" and reactions discussed in the lecture portion of the course, as well successful completion of a multistep reaction. Each lab uses some type of spectroscopy to determine the success of the reaction and product purity. Students are required to discuss their results in written format. All labs are conducted in a wet-lab and are hands-on.
TEXTBOOK / SPECIAL MATERIALS:
- Lab 1
- Safety & Procedures
- Students will review safety information, laboratory policies and procedures.
- Lab 2
- Students will interpret spectral data from multiple types of spectroscopy to elucidate chemical
- Lab 3
- Grignard Reagents
- Students will study and perform a Grignard reaction.
- Lab 4
- Alcohol Oxidation
- Students will oxidize a secondary alcohol with the Jones reagent to form a ketone.
- Lab 5
- Aldol Condensation
- Students will complete a base catalyzed aldol condensation and subsequent dehydration to form an
- Lab 6
- Ester Synthesis
- Students will prepare an ester via Fischer esterification from an alcohol and carboxylic acid after
first using analytical methods to determine the identity of an unknown alcohol and carboxylic acid.
- The scent of their ester will determine if their unknown identification was correct.
- Lab 7
- Friedel Crafts Acylation
- Students will perform an acid-catalyzed acylation of ferrocene with acetic anhydride.
- Lab 8
- Nucleophilic Aromatic Substitution
- Students will explore the activating and deactivating effects of a disubstituted benzene on
- Lab 9
- Selective Reduction to Amines
- Students will complete and compare two chemoselective reduction reactions on 4-nitroacetanilide to
form an amine.
- Lab 10
- Aspirin Synthesis
- Students will complete the synthesis of the analgesic, aspirin, from salicylic acid and acetic
- Labs 11-13
- Multistep Synthesis of Nylon-6,6
- Students will synthesize nylon-6,6 starting from cyclohexanol
Text: Organic Chemistry by Francis A. Carey & Robert M. Giuliano, 10th edition. This text will be used daily in class, as well as for homework assignments and general reference.
Lab Manual: CHEM 134 Lab Manual. A.J. Gaier. DACC custom lab manual. Fall 2017 edition.
Laboratory Notebook: A bound laboratory notebook with duplicate sheets will be used to record data in lab. The recommended version is the spiral-bound, 100 page carbon copy notebook from Hayden McNeil Publishers.
Safety Goggles: Students must purchase their own laboratory safety goggles and are available in the DACC bookstore. They must be splash goggles with the side protection and NOT safety glasses. Acceptable eyewear will have "Z87" stamped on the side.
Calculator (Optional): Any simple scientific or graphing calculator is sufficient. A calculator may only be necessary for small portions of the class.
Enclosed Shoes & Pants: For lab days. If you are not dressed properly you will not be allowed to participate.
See bookstore website for current book(s) at https://www.dacc.edu/bookstoreEVALUATION:
Grading is based on a weighted percentage of five different categories with overall grade divisions at 90, 80, 70 and 60 percent. The five categories are:
|four or more midterm tests
fifteen lab reports
eight to ten quizzes
Attendance is required and a student may be withdrawn from the class roster due to unexcused absences
Laboratory work must be performed during the regularly scheduled laboratory period. “Make-up” laboratory work at an alternate time will not be an option. No credit will be given for laboratory reports submitted if the student was absent from the laboratory session. If a student has a valid excuse for missing a lecture or a laboratory class, credit for the missed period may be arranged with the instructor and will not be automatically given to the student.
|STUDENT CONDUCT CODE:||Membership in the DACC community brings both rights and responsibility. As a student at DACC, you are expected to exhibit conduct compatible with the educational mission of the College. Academic dishonesty, including but not limited to, cheating and plagiarism, is not tolerated. A DACC student is also required to abide by the acceptable use policies of copyright and peer-to-peer file sharing. It is the student’s responsibility to become familiar with and adhere to the Student Code of Conduct as contained in the DACC Student Handbook. The Student Handbook is available in the Information Office in Vermilion Hall and online at: https://www.dacc.edu/student-handbook|
|DISABILITY SERVICES:||Any student who feels s/he may need an accommodation based on the impact of a disability should contact the Testing & Academic Services Center at 217-443-8708 (TTY 217-443-8701) or stop by Cannon Hall Room 103. Please speak with your instructor privately to discuss your specific accommodation needs in this course.|