ORGANIC CHEMISTRY CH 225-FALL 2004
LECTURE - MWF 11:00 – 11:50 CRAWFORD HALL 207
LAB – MW –2:00 – 4:50, T 9:00-11:50 CRAWFORD HALL 335
Instructor: Dr. Judy Westrick
Office: Crawford Hall 318 ex. 2165 E-mail: jwestrick@lssu.edu
Office Hours: 9:00-9:50 M, 1:00-1:50 MTWF and by appointment
Required Textbooks and Class Materials: McMurry, Organic Chemistry, Lehman Operational Organic Chemistry 1 st
Edition, Molecular Model Kit for Organic Chemistry
State Council of State Science Supervisors:
http://www.csss-science.org/safety.shtml
http://www.csss-science.org/downloads/scisafe.pdf
This class is an introduction to organic chemistry. The objectives of this class are to master fundamental organic
chemistry concepts.
Chapter 1
-Review definitions – atom, covalent bonds, polar bonds, electron configuration, wavefunction, valence
electrons.
-Construct Lewis Structures, bonding and nonbonding electrons.
-Valence bond theory, sigma bonds and pi bonds.
-Hybridization of s and p orbitals.
-Molecular Orbital Theory, bonding MO and antibonding MO.
Chapter 2
-Review the electronegativity trend using the Periodic Table.
-Predict polar covalent bonds, dipole moments, and formal charges.
- Understand the concept of resonance forms, rank the importance of various resonance forms, and
draw each of the resonance form.
-Review Bronsted-Lowry acid/base chemistry; predict acid-base reactions from pKa values.
-Lewis acid/base chemistry.
-Drawing chemical structures.
Chapter 3
-Overview on classification by functional groups; carbon-carbon multiple bonds, carbon singly bonded to
an electronegative atom, carbonyl groups
-Define and identify constitutional isomers.
-Name alkanes and cycloalkanes.
-Understand the basic physical and chemical properties of alkanes and cycloalkanes.
Chapter 4
-Understand how different conformational isomers have different energies. Predict high and low energies
by using energy cost such as torsional, steric, and angle strains.
-Special attention will be spent on the conformation of cyclohexane. Predicting most stable conformation
by using the torsional and steric strains.
-Overview on conformational polycylic molecules.
Chapter 5
-Overview of basic organic reactions, addition, elimination, substitution, and rearrangement reactions.
-Define reaction mechanism and the types of bond cleavage.
-Overview on radical reactions and its steps, initiation, propagation, and termination.
-Overview on polar reactions and be able to predict the nucleophile and electrophile
-Chemical reactions can be described through equilibria, rates and energy changes. Equilibria, kinetic and
bond dissociation equations will be reviewed. Interpreting and creating energy diagrams.
Chapter 6
-Structure and reactivity of alkenes will be discussed. Review basic sp2 hybridization.
-Calculating a molecules degree of unsaturation.
-Learn the alkene nomenclature including cis/trans and E/Z designation of isomers.
-Predict the stabilities of substituted alkanes.
-The mechanism of electrophilic additions of HX to alkenes will be review. This reaction is regiospecific
and uses Markovnikov’s Rule. Hammond postulate and carbocation rearrangement also be introduced at
this time.
Chapter 7
-Study the alkene reactions. Use concepts such as molecular geometry and polarity to predict reaction
products.
-Alkene-forming elimination reaction – dehydrohalogenation and dehydrations
-Study the alkene addition reactions. This will include basic reactions such as addition of halogens,
halohydrin formation, oxymercuration, hydroboration, carbenes
-Learn the reaction mechanism for reduction, oxidation, cleavage of alkenes.
-Learn the reaction mechanism for the addition of radicals to alkenes.
Chapter 8
-Review the structure of alkynes.
-Learn how to name alkynes.
-Study the reaction mechanism of the elimination of dihalides to make alkynes.
-Study the alkene reactions such as the addition of HX and X2, hydration, reduction, and oxidative cleavage.
-Use acid/base chemistry to form the acetylide anion for alkylation.
-Introduction to synthesis. This is a great way to reinforce all of the chemical reactions you have learned.
Chapter 9
-Stereochemistry is the study of handedness. Define enatiomers, chirality and optical activity.
-Learn how to assign chiral center the proper rotational configuration. R or S instead of right or -left,
respectively.
Chapter 10
-Review how to name alkyl halides.
-Use periodic trends to predict bond length, strength, and dipole-moment.
-Review, electrophic addition reactions and radial addition of halogens, and apply the Hammond postulate
to predict reaction rates and product yield.
-Determine if an organic reaction is oxidation, reduction or neither.
Chapter 11
-Able to predict if a nucleophilic substation is (Sn2, Sn1, E2 or E1). In order to determine which
mechanism, the student must be able to evaluate the steric effects of the alkyl halide, strength of the
nucleophile (nucleophilicity), the readiness of the leaving group, and solvent charactersics.
-Must be able to apply Zaitsev’s Rule to elimination reactions.
-Predict products the stereochemistry of a nucleophilic type reaction.
Chapter 12 and 13
-Known what mass, infra red (IR), Nuclear Magnetic Spectroscopy (NMR) spectrometries measure and the
basic concepts which they work.
-Interpret spectra.
Class Schedule
Dates
Aug 30, Sept 1
1. Structure and Bonding
Sept 3, 8
2. Polar Bonds and Their Consequences
Sept 10, 13, 15
3. Organic Compounds: Alkanes and Cycloalkanes
Sept 17, 20, 22
4. Stereochemistry of Alkanes and Cycloalkanes
Sept 24
Exam 1, 2, and 3
Sept 27, 29, Oct 1
5. Overview of Organic Reactions
Oct 4, 6, 8
6. Alkenes: Structure and Reactivity
Oct 11, 13, 15
7. Alkenes: Reactions and Synthesis
Oct 20
Exam II Chapters 4, 5 and 6
Oct 18, 22, 25
8. Alkynes: Introduction to Organic Synthesis
Oct 27, 29, Nov 1,3
9. Stereochemistry
Nov 5, 8
10. Alkyl Halides
Nov 15
Exam III Chapters 7, 8, 9,10
Nov 10, 12, 17, 19
11. Reactions of Alkyl Halides: Nucleophilic Substitution and
Eliminations
Nov 22, 29
12. Structure Determination: Mass Spectroscopy and Infrared
Spectroscopy
Dec 3, 6, 8
13. Structure Determination: NMR
Dec 1
Exam V 11, 12
Monday, Dec 13, 2003 10 – 12
Final Exam
All make up exams will be oral.
TENTATIVE LABORATORY SCHEDULE
Important: You must come to your scheduled lab period during the week of Aug 30th or notify me if you will be
absent. Otherwise you may be removed from the course.
Exercises to be completed will be assigned or provided on the handouts. All labs are worth 10 points.
Weeks
1
2
3
4
5
6
7
8
9
10
11
12
13
14
Experiment
Safety and equipment review
NO LABS
Food Preservative
Model Worksheet
Separating "Panacetin"
Identifying "Panacetin" Component
Salicylic Acid
Stereochemistry Model Worksheet
Synthetic Banana Oil
Camphor
Lycopene from Tomato Paste
Constituent of Clove Oil
Preparation and Distillation of
Cyclohexene
Clean Lab and Final Exam
To Turn In
Report week
benzoic acid
Worksheet
Aspirin
Unknown
salicylic acid
Worksheet
isopentyl acetate
Camphor
lycopene solution
clove oil
IR and cyclohexene
2
4
4
6
7
8
8
10
11
12
13
14
Lab Rules and Safety. WEAR YOUR SAFETY GOGGLES IN THE LAB AT ALL TIMES. You should also wear
your gloves and aprons while handling chemicals. You must comply with the safety rules posted in the lab; repeated
violation of these rules may result in expulsion from the course with a grade of F. Do not carry out any unassigned
experiment or project without written authorization by the instructor. Laboratory work is to be performed during
scheduled lab periods only (see the instructor for information about making up labs). The prep room and chemical
storage area are off limits to students, except authorized laboratory assistants.
Preparations. YOU MUST TURN IN THE SPECIFIED PRODUCT FROM EACH EXPERIMENT. Each product
listed in the lab schedule should be submitted to the instructor on or before the due date for the experiment.
Lab Reports. Turn in each lab report on the form provided on or before the due date attaches any required graphs or
spectra. Reports must include answers to the assigned exercises. Late reports are penalized 3 points if turned in
within a week after the due date, 10 points thereafter.
Point System
#
Type
Points
Total Points
4
Hour exams
Quizzes, Assignments
Final
125
500
100
200
Lab
Lab Final
Week of Dec 15
13
130
70
Total
1000
1
Lab
13
200
Straight grading scale:
90% and higher A, 80%-89% B, 70%- 79% C, 60% - 69% D, below 60% F
Disability Services and Accommodations for Students. In compliance with Lake Superior State University policy
and equal access laws, disability-related accommodations or services are available. Students who desire such
services are to meet with the professor in a timely manner, preferably the first week of class, to discuss their
disability-related needs. Students will not receive services until they register with the Resource Center for Students
with Disabilities (RCSD). Proper registration will enable the RCSD to verify the disability and determine reasonable
academic accommodations. RCSD is located in South Hall Office 206. The telephone number is (906) 635-2454.
Academic Misconduct: Scholastic misconduct is cause for a failing grade, and I reserve the right to place a letter
about the incident in the student’s permanent file in the Office of Academic Affairs. Scholastic dishonesty includes,
but is not limited to, cheating on assignments or examinations, plagiarizing, misrepresenting as your own work any
part of work done by another, or interfering with another student’s work.
Finally, this syllabus is my best estimate of the topics we will cover. I reserve the
right to modify this syllabus as I see fit during the course of the semester.