CHEM 2223 – Organic Chemistry I
Course Description:
Fundamental concepts of nomenclature, formulae, preparation and properties of organic compounds. Modern electronic and
molecular orbital theories are introduced. Laboratory experiments illustrate properties and preparation of organic
compounds.
Prerequisites:
CHEM 1110 (curriculum change to require CHEM 1210 as prerequisite is pending, Oct. 2009)
Required Text:
Organic Chemistry (2 nd Edition), Janice Gorzynski Smith, McGraw Hill 2008
Instructional Objectives:
This course in Organic Chemistry builds on students’ understanding of fundamental principles developed in General
Chemistry, including descriptions of chemical bonding, the significance and quantitative analysis of chemical
thermodynamics, chemical kinetics including reaction rate expressions, properties of gases and solutions, descriptions of
acidity and basicity, chemical equilibria, and the chemistry of oxidation and reduction processes.
Learning objectives during first semester Organic Chemistry include student understanding of:
1.
The geometries and structures of carbon-based compounds, the tetravalence of carbon atoms, and the local
geometries that result from sp, sp 2, and sp 3 hybridization.
2.
The common and important functional groups in organic compounds.
3.
The composition and structures of hydrocarbon compounds and geometric isomerism.
4.
Stereoisomerism; chirality of tetra-substituted carbon atoms; R and S enantiomers; and diastereoisomerism.
5.
The standard organic chemistry reaction mechanisms: substitution, elimination, and addition reactions.
6.
The preparation, structures, and reactions of alkyl halide compounds. The reactivity of electron deficient carbons.
Nucleophilicity and structures of nucleophiles.
7.
The preparation, structures, and reactions of alkene and alkyne compounds.
8.
The fundamental description of spectroscopic methods of analysis including mass spectrometry, infrared, and
nuclear magnetic resonance spectroscopy. Determinations of chemical structure on the basis of spectroscopic
evidence.
Instructional Objectives of the Laboratory Component of CHEM 2223:
1.
Safe and effective laboratory practice, use of personal protective equipment, handling of potentially hazardous
chemicals, appropriate handling of hazardous waste materials. Effective methods of recording experimental
procedures, including preparative methods and responsible management of experimental data.
2.
Fundamental methods of laboratory separations: thin layer chromatography, recrystallization, simple and
fractional distillation, and simple methods of preparative chemistry, refluxing reaction mixtures, and controlled
chemical transformations.
3.
Introduction to hands-on experience with FTIR and NMR spectrometers.
Assessment:
Evaluation Methods and Criteria
Students’ progress will be evaluated through success in solving homework exercises, laboratory experiments, and their
written reports of laboratory work. The final grade will be a weighted average of grades earned on mid-term exams,
homework, laboratory work, and a final exam. The distribution is as follows:
Three mid-term exams
Laboratory work
Homework and in-class quizzes
Final exam
50%
25%
5%
20%
Course Outline:
Week 1: Introduction to organic chemistry; how to study and learn organic chemistry: see Forward, Contents, P reface, and
P rologue to Smith text. Review of general chemistry: bonding, acid-base chemistry; equilibrium expressions.
Week 2: Lewis structures, molecular shapes; line-angle formulas for organic molecules, nomenclature.
Week 3: Acids and bases; organic acids and conjugate bases.
Week 4: Introduction to organic functional groups and their chemistries.
Week 5: Review and Exam 1
Week 6: Alkanes, conformations of ethane, butane, and cyclohexanes; oxidation of alkanes.
Week 7: Stereochemistry; enantiomers, R and S configurations; diastereomers.
Week 8: Review and Exam 2.
Week 9: Introduction to organic reactions, including appropriate use of thermodynamic functions, energy diagrams, and
rate expressions.
Week 10: Introduction to spectroscopic identification of organic compounds.
Week 11: Alkyl halides, C-X bond polarity; leaving groups; nucleophilicity and basicity; nucleophilic substitution.
Week 12: Elimination reactions; E1 and E2 mechanisms.
Week 13: General review and Exam 3.
Week 14: The chemistry of alcohols, ethers, and epoxides.
Week 15: P reparation and reactions of alkenes; preparation and chemistry of alkynes.
Week 16: Review and final exam.
Laboratory work: 3 hours per week
Experiment 1: Safety and responsibility in the lab; preparation for labs; notebook keeping; preparation of lab reports
check-in.
Experiment 2: Melting point determinations.
Experiment 3: Crystallization and purification of organic materials.
Experiment 4: Distillation (microscale) fractional distillation.
Experiment 5: Acid-base extractions.
Experiment 6: Gas-liquid chromatography.
Experiment 7: Thin layer chromatography.
Experiment 8: Introduction to mass spectrometry and infrared spectroscopy; reading spectra.
Experiment 9: Nuclear magnetic resonance spectroscopy.
Experiment 10: SN2 reaction: 1-bromobutane.
Experiment 11: P reparation of alkenes from alcohols.
Experiment 12: Chemical information resources; literature searching.
Experiment 13: Chemical computation.
Experiment 14: Laboratory preparation and analysis of aspirin.
Experiment 15: Complete all work; check out.
Laboratory Course Policies:
G rade: Your grade for laboratory work will be computed from 2 factors:
(i)
(ii)
Written reports of laboratory work, due at the start of the following lab session. Reports will be graded from
0 to 10. Reports that are late may receive a maximum of 5. (ca. 90% of your lab grade)
Laboratory technique, including your preparedness and participation in each exercise. Good note-keeping
and working as colleagues with partners will enhance your grade. (ca. 10% of your grade)
Attendance and Preparation: One absence from the lab will be excused; your 11 best grades will be used in computation
of your lab grade. If you miss more than 2 labs, your instructor may give you a grade of WF.
Read and plan your work before lab; arrive on time. Instructors usually give an overview and description of the lab
exercise at the start of each session. These are valuable to the success of your lab. Repeated lateness will detract from your
grade.
Personal Protective Equipment: Our department requires that students wear lab coats and safety glasses while in labs.
The labcoat and safety glasses requirement begins on the second week of the semester. You must wear safety glasses at all
time that any lab work is underway. Do not make excuses for not protecting your eyes. Failure to observe safety glasses
policy may result in your being dismissed from the lab.