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| CHEM133 syllabus
|COURSE NUMBER: ||CHEM133|
|COURSE TITLE:||Organic Chemistry I |
|IAI CODE(S):|| CHM 913|
|SEMESTER CREDIT HOURS:||5|
|CONTACT HOURS:||Lecture 3 / Lab 4|
Face to Face|
This course is the first semester of a two-semester sequence in Organic Chemistry for students pursuing chemistry, biochemistry, medical or engineering professions. Topics covered are meant to build basic skills and knowledge in nomenclature, functional groups, molecular structure and analysis, reactivity and synthesis. Laboratory is required and covers the general techniques needed in organic synthesis and spectroscopic analysis methods. The lecture meets three hours per week and the lab is four hours per week.
A lab is required for this course. Some sections will require a separate lab, while other sections will include the lab.
COURSE OBJECTIVES / 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:
- Alkanes and cycloalkanes
- Alkyl halides
- Alkadienes and allylic systems
- 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 and spectroscopic techniques such as Thin Layer Chromatography, melting and boiling point determination, gas chromatography, IR 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.
Weekly Lab Outline -
- Chemical Bonding (15%)
- Introduction to organic chemistry and its compounds
- Major function groups
- common and IUPAC systematic
- Physical properties (such as intermolecular forces, melting point and boiling point) and their relation to solubility and structure
- Polarity of molecules and dipole moments
- Bonding in organic compound
- covalent and ionic
- Hybridization - sp3, sp2 and sp
- Acid-base theories
- Arrhenius, Bronsted-Lowry and Lewis
- Formal charge and oxidation state
- Structural formulas
- Alkanes (10%)
- Classes of hydrocarbons and functionally substituted derivatives of alkanes
- Constitutional isomers and nomenclature
- Physical properties of hydrocarbons
- Formation, chemical reactions and thermochemistry of hydrocarbons
- Conformations of Alkanes and Cycloalkanes (10%)
- Conformational analysis as depicted by the commonly used representations
- Chair and boat conformations of cyclohexane
- Heterocyclic compounds and their properties
- Alcohols and Alkylhalides (10%)
- Nomenclature and structure (primary, secondary and tertiary alcohols)
- Solubility and hydrogen bonding
- Bronsted acid-base theory and pK values
- Proton transfer theory
- Reactions and mechanisms
- Free radical chlorination of methane
- Alkylhalides from alcohols and the SN1 mechanism
- Heats of reaction
- Alkenes: Elimination and Addition Reactions (10%)
- Nomenclature, structure and physical properties
Dehydration of alcohols and Zaitsev's Rule
- Dehydrohaligenation of alkylhalides
- Mechanism and stereochemistry elimination and addition
Electrophilic addition and Markovnikov's Rule
- Free radical addition: Anti-Markovnikov orientation
- Hydroboration-oxidation, halohydrin formation and ozonolysis
- Stereochemistry (10%)
- Enantiomers and chiral molecules
- Specific rotation and polarimetry
- R and S configurations
- Conformational and configurational isomerism
- Rate of mutarotation of glucose
- Reactions which form stereogenic centers
- Chiral molecules with multiple stereogenic centers
- Nucleophilic Substitution (10%)
- Relative reactivity of leaving groups and nucleophiles
- SN2 and SN1 reactions and their mechanisms and stereochemistry
- Effects of structure and solvent polarity on reaction rates
- Substitution reactions and their corresponding competitive elimination reactions
- Alkynes (5%)
- Structure, formation and nomenclature
- Relative acidity of acetylene
- Alkylation, elimination and addition reactions
- Dienes (5%)
- Allylcations and free radicals and their reactions
- Conjugation and electron delocalization
- 1,2- versus 1,4-addition reactions
- Diels-Alder reaction
- Molecular orbitals of polyenes
- Arenes and Aromaticity (10%)
- Structure and resonance stability
- Nomenclature of benzene and its derivatives
- Aromaticity and
- Electrophilic aromatic substitution
- Directing effects of substituent groups
- Mechanism of substitution and the benzenonium ion
- Inductive and resonance effects on orientation
- Substitution on ring verses side chain for arenes
- Spectroscopy (5%)
- Background and methods for use of gas chromatography, ultraviolet and infrared spectroscopy
- Use of gas chromatography, ultraviolet and infrared spectroscopy in the lab section for product analysis and purity assessment
Experiments completed in this semester teach basic techniques for synthesis and analysis. Spectroscopy is used where applicable 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, as well as laboratory policies and procedures.
- Lab 2 - Melting Point & Boiling Point - Learn how to accurately determine melting points and boiling point to identify an unknown.
- Lab 3 - Recrystallization - Purify a sample based on simple recrystallization techniques.
- Lab 4 - Separation by Extraction - Separate a mixture of water soluble and organic soluble components through extraction.
- Lab 5 - Thin Layer Chromatography - Examine the relative polarities of compounds using thin layer chromatography.
- Lab 6 - Column Chromatography - Isolate different components of a mixture with basic flash chromatography.
- Lab 7 - IR Spectroscopy - Determine the identity of an unknown compound through infrared spectroscopy analysis.
- Lab 8 - Isolation of Caffeine from Tea (Part I) - Extract caffeine from a sample of tea leaves and isolate the crude material.
- Lab 9 - Isolation of Caffeine from Tea (Part II) - Purify crude caffeine by sublimation.
- Lab 10 - Distillation & Gas Chromatography - Distill a mixture of organic liquids and analyze the distillate with gas chromatography.
- Lab 11 - SN1 Substitution - Examine the SN1 mechanism and rate of reaction.
- Lab 12 - SN2 Substitution - Examine the SN2 mechanism and rate of reaction.
- Lab 13 - Bromine Addition - Examine a reaction of electrophilic addition to an alkene.
- Lab 14 - Dehydration of Cyclohexanol - Examine a simple elimination reaction of an alcohol to an alkene.
- Text: Organic Chemistry by Francis A. Carey & Robert M. Giuliano, 8th edition. This text will be used daily in class, as well as for homework assignments and general reference.
- Lab Manual: CHEM 133 Lab Manual. A.J. Gaier. DACC custom lab manual. Fall 2016 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 eye ware 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.
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 accounting for forty percent of the course grade, fifteen lab reports accounting for twenty percent of the course grade, ten quizzes accounting for ten percent of the course grade, classroom work accounting for ten percent of the course grade, and a final exam accounting for twenty percent of the course grade. 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.Notes:
All students must pass the laboratory portion of the class in order to pass the course.
The final exam will include all material covered in the semester. Every student is required to take the final exam at the scheduled time. Each student must take and pass the cumulative final in order to pass the course.
A curve may be applied at the instructor's discretion.