MARYVILLE UNIVERSITY COURSE SYLLABUS
Semester/Year:           Fall 2008
Course:                       CHEM 203 Organic Chemistry I
Credit Hours:              4
Meeting Days:            CHEM 203 01 Lecture              MW     8-9:15 a.m., R 2317
                        CHEM 203 L1 Lab 1                 M         12:15-2:55 p.m., K 2117
                        CHEM 203 L2 Lab 2                 W         12:15-2:55 p.m., K 2117
Professor:        Dr. Frank Stary
Office Phone:  529-9425
Office Hours:  MW  9:25 a-12:05 p and M T W 10:50 a-12:05 p in R 3306 and other times by appointment, or just drop by and talk. My schedule is near the door of my office.
Objective: To introduce the student to alkanes, stereochemistry, alkyl halides, alcohols and ethers, alkenes, dienes and alkynes. Assigned problems give the student experience necessary to understand organic chemistry and the tests given in the course. These problems are graded to give the students feedback on their progress. There is an emphasis on reactions and a small amount of mathematics in the lectures and the examinations.
Text Books: Morrison & Boyd Organic Chemistry, Sixth Ed.
Study Guide to Morrison & Boyd Organic Chemistry, Sixth Ed. (Optional Answer Book)
Mayo, Pike, Butcher Microscale Organic Laboratory, 3rd Ed.
Bound Lab Notebook (not returned), Safety Glasses, Calculator
Technology: Digital melting point apparatus, refractometer, Microscale glassware kits, analytical balances, gas chromatography, IR spectrometer, automatic pipettes, top-loader balances, calculator, sublimation apparatus demonstration, vacuum pump demonstration and magnetic hot plates

NOTE:  This syllabus is subject to change at the discretion of the professor to accommodate instructional and/or student needs.           
Labs:   1 Measurement of Physical Properties
2 The Separation of a 5 mL Mixture of Heptanol (bp 153 ^oC) and Cyclohexanol (bp 160 ^oC) by Gas Chromatography
3A Simple Distillation at the Semimicroscale Level: Separation of Ethyl Acetate from trans-1,2-Dibenzoylethylene
4A Determination of a Partition Coefficient for the System Benzoic Acid, Methylene Chloride and Water
5A Reduction of Cyclohexanone to Cyclohexanol Using a Metal Hydride Reagent
6A Purification of trans-1,2-Dibenzoylethylene
7 The Cannizzaro Reaction with 4-Chlorobenzaldehyde: 4-Chlorobenzoic Acid and 4-Chlorobenzyl Alcohol
8A The Esterification Reaction: Ethyl Laurate
9 The E1 Elimination Reaction: Dehydration of 2-Butanol to Yield 1-Butene, trans-2-Butene and cis-2-Butene
11B Demonstration of the Purification of Caffeine by Sublimation
One week after the experiment is performed, the lab report is submitted for grading by the professor. It is best to turn it in before the lab in the morning so you can get ti back in the lab. The format, shown on page 39 of the lab textbook (Mayo) gives the student practice in writing technical reports.
Lecture Homework:
Chapter            Chapter Topics and Problems                                         
1          Structure and Properties 1df  2eh  3ah  5ae  9de  13f
2          Methane Energy of Activation. Transition State 1y  3f  6  11e  12
3          Alkanes Free Radical Substitution 1dg  2fk  write no. of Me, Et, nPr, iPr, secBu (for probs. to the left) 7  8ae  9c  10c  11c  18
4          Stereochemistry I. Stereoisomers 1gkoqst  6e  7a 8a
5         Alkyl Halides Nucleophilic Aliphatic Substitution 1e  2d  3aef  4acde  5abh  6a  7a
6          Alcohols and Ethers 2cf  3c  4  6ceghl (skip names)  7ace (do not bal., show prod) 12a  17e
8           Alkenes I. Structure and Preparation Elimination 1e  2e  3d  5acdef (do not bal.) 6f  8a  9a
9           Alkenes II. Reactions of the Carbon-Carbon Double Bond Electrophilic and Free-Radical Addition 1abefijklmnoqrst (skip names) 2a 16bef  17ak
11         Conjugation and Resonance Dienes 3 (skip names) 8
12         Alkynes 2abd  3fik  4agjmo  7h  9
EXPECTED LECTURE SCHEDULE
Aug      27
            29         Cha 1 due
Sep       05         Cha 2 due
            10        
            12         Exam 1 Chas 1 & 2
            17        
            19         Cha 3 due
            24         Cha 4 due                                
            26        
Oct       01         Exam 2 Chas 3 & 4
            03        
            08         Midterm Exam Chas 1-4
            10        
            15         Cha 5 due
            17         Cha 6 due
            22        
            24         Exam 3 Chas 5 & 6
            29        
            31         Cha 8 due
Nov      05         Cha 9 due
            07        
            12         Exam 4 Chas 8 & 9
            14        
            26         Cha 11 due
            28         Cha 12 due
Dec      03         Exam 5 Cha 11 & 12
            05        
            10        Final Exam Chas 5,6,8,9,11 and 12 TBA: Do not buy airplane tickets departing before 6 pm on 10 Dec 07.