BRAZOSPORT COLLEGE LAKE JACKSON, TEXAS SYLLABUS CHEM 2423 - ORGANIC CHEMISTRY CATALOG DESCRIPTION: CHEM 2423 Organic Chemistry I. CIP 4005045203 A study of the nomenclature, classification and reactions of aliphatic compounds by means of reaction mechanisms, transition state theory, stereochemistry. Alkanes, alkyl halides, alcohols, alkenes, alkynes, alicyclics and aromaticity are studied. (4 SCH, 3 lecture, 3 lab) Prerequisite: A grade of C or better in CHEM 1412. Required skill level code: Reading, A; Writing, A. Judy Chu Mickey McGaugh Kirby Lowery Gary Hicks Ken Tasa June 2010
BRAZOSPORT COLLEGE SYLLABUS CHEM 2423 - ORGANIC CHEMISTRY II. Course Evaluation Student Evaluation One hour exams are designed to measure the student's mastery of the course objectives. Take home quizzes are designed to indicate whether or not the student is doing the assigned reading carefully. Pre-laboratory questions are intended to measure the student's laboratory techniques, understanding of experiments done, and how the student can apply concepts covered in lecture to practical situations. The pre-laboratory questions count toward the experiment grade. The laboratory grade will be the average of the experiment grades. The course grade will be determined from the following: Exam average 60-70% Lab average 20-25% Take home quizzes 10-15 % TOTAL 100% Each instructor will announce the exact percentages to be used at the beginning of the course. Instructor Evaluation A. Students will be given an opportunity to evaluate their instructor and the course content. B. Instructor will review and evaluate in terms of withdrawal rate. C. Final grades given will be reviewed in an effort to determine if a pattern of high or low grades exists. Department Evaluation A. Faculty and the Division Chair will review student s grade and withdrawal trends. B. Faculty and the Division Chair will review the Course, Competencies, and Perspectives Assessment 2
BRAZOSPORT COLLEGE SYLLABUS CHEM 2423 - ORGANIC CHEMISTRY III. COURSE CONTENT Objectives The course is designed to help the student: 1. To become familiar with the nomenclature of the various major families of hydrocarbons: alkanes, alkyl halides, alcohols, alkenes, alkynes, and alicyclics. 2. To understand how chemical bonding and molecular structure in hydrocarbons are related to physical properties and chemical behavior. 3. To gain a basic understanding of stereoisomers, their relationship to optical activity, and their application to the elucidation of reaction mechanisms. 4. To learn the various reaction mechanisms which are characteristic of each of the functional groups in the hydrocarbon families, as well as the structures and conditions which favor one mechanism over another. 5. To understand the application of reaction kinetics and transition state theory to the prediction of the most likely products for a given set of reagents. 6. To understand the special stability of benzene and its derivatives in terms of electron delocalization and basic molecular orbital theory. 7. To gain a background in chemical principles sufficient for success in more advanced courses such as Chemistry 2425. 8. To acquire basic laboratory skills and carry out quantitative procedures in a laboratory setting as specified in section III. 3
Laboratory Objectives YOU MUST MAKE AT LEAST A D IN THE LABORATORY PORTION OF THIS COURSE IN ORDER TO PASS THE COURSE. Given the proper laboratory equipment and reagents, the student will: 1. Determine the melting points of pure compounds and mixtures of variable composition and draw a melting point curve for the mixtures. 2. Demonstrate the purification of a solid by recrystallization. Sufficient purity is shown by a melting point range not exceeding 2 C. 3. Separate a mixture of an organic acid, and a neutral compound by successive basic and neutral extractions. 4. Demonstrate the purification of a liquid by simple and fractional distillation, and determine its approximate composition from the distillation graph. Determine the purity of the various cuts by refractive index. 5. Separate camphor from B-carotene by sublimation. Determine the purity by melting point and UV-Vis spectroscopy 6. Isolate Clove Oil from Cloves Using Steam Distillation. Characterize the product via infrared spectroscopy. 7. Synthesize an alkene from an alcohol by the dehydration mechanism and purify the product. Yield should be greater than 60%. 8. Perform an electrophilic addition reaction on an alkene and purify the product. Yield should be greater than 60%. 9. Separate a Mixture of esters by Gas Chromatography. Determine the composition of an unknown mixture. 10. Nucleophilic substitution, factors effecting the rate and synthesis of 1-bromobutane. 4
Outline CHEM. 2423 LECTURE SCHEDULE * Week Topic 1 Review of Bonding 1.1-1.1.13 Hybridization and Acids/Bases 1.14-1.21 2 Nomenclature of Organic 2.1 2.7 Compounds 3 Physical Properties of Organic 2.8-2.10 Compounds, Conformation of Alkanes Conformation of Cycloalkanes 2.11-2.15 4 Exam 1 Alkenes - structure, nomenclature & 3.1-3.7 reactivity 5 Reaction of Alkenes 4.1-4.6 Reaction of Alkenes (continued) 4.7-4.12 6 Exam 2 Stereochemistry 5.1-5.8 7 5.9-5.14 Stereochemistry (continued) 5.18-5.19 Reaction of Alkynes 6.1-6.8 8 Alkynes (continued) 6.9-6.12 Exam 3 9 Electron Delocalization and 7.1-7.8 Resonance Consequences of Electron Delocalization Dienes 7.9-7.10 8.1-8.5 10 Reaction of Dienes 8.6-8.13 Reactions of Alkanes 9.1-9.5 11 Reactions of Alkanes (continued) 9.6-9.9 and review Exam 4 12 Substitution Reactions of Alkyl 10.1-10.6 Halides Stereochemistry of S N 1 & S N 2 10.7-10.11 reactions 13 Elimination Reactions 11.1-11.7 14 Elimination vs. Substitution 11.8-11.12 Reactions of Alcohols 12.1-12.5 5
15 Reactions of Ethers, Organometallic Compounds Exam 5 12.6-12.12 16 Final Exam *This schedule is subject to change. CHEM. 2423 LAB SCHEDULE * Week Experiment Organic Laboratory Techniques Reading 1 No Lab 2 (No Lab) 3 Check-in and T-700 Lab Safety pp1-12 4 T-701 Melting Points of Compounds and Mixtures pp. 13-24 5 T-703 Purifying Acetanilide by Recrystallization pp. 25-36 6 T-704 Separation of Cyclohexane and Toluene by Distillation pp. 37-52 7 T-705 Separation of Acids and Neutrals by Extraction pp. 53-68 8 Catch-up / Make-up 9 T-722 Isolating Clove Oil from Cloves Using Steam Distillation pp. 137-151 10 R-712 Dehydrating Cyclohexanol pp 93-107 11 S-719 Brominating Alkenes pp125-135 12 R-714 Nucleophilic Substitution - Synthesis of 1- bromobutane Pp109-123 13 R-714 Nucleophilic Substitution - Factors Affecting S N 1 Reactions 14 T-709 Separating Mixtures by Gas Chromatography pp. 81-92 15 Make-up, Cleanup and Check out * The schedule is subject to change. Changes will be announced in class. The schedule will vary from semester to semester. The above schedule is based on a 16 week schedule where each week equates to 6 contact hours. In summer sessions the schedule will be adjusted to have more contact hours per week to accommodate the shorter semester. 6
BRAZOSPORT COLLEGE SYLLABUS CHEM 2423 - ORGANIC CHEMISTRY IV. LEARNING OUTCOMES CHEM 2423 OUTCOME Write the common or systematic name of the common classes of organic compounds from a structural drawing or given the common name or systematic name of the common classes of organic compounds, draw the structure of the compound. Choose the lowest (or highest) energy conformation of an acyclic or cyclohexane derivative from several choices. Draw the correct structure for the reaction product(s) for the addition of electrophylic reagents to an alkene or given the alkene and the reaction product, state the reagents required for the transformation. Given the structure of a chiral compound, correctly state its absolute configuration or given the name of a chiral compound including its absolute configuration, draw its structure. For compounds containing delocalized electrons, draw the Lewis structure of resonance contributors (including formal charges) and predict their relative stabilities. METHOD OF ASSESSMENT the final exam which relate to naming or drawing the structure of the common classes of organic compounds will be evaluated: 3, 4 and 5. the final exam which relate to choosing the lowest (or highest) energy conformation of an acyclic or cyclohexane derivative will be evaluated: 7 and 8. the final exam which relate to drawing the correct structure for the reaction product(s) for the addition of electrophylic reagents to an alkene or given the alkene and the reaction product, stating the reagents required for the transformation will be evaluated: 11, 12, and 13. the final exam which relate to given the structure of a chiral compound, correctly stating its absolute configuration or given the name of a chiral compound including its absolute configuration, drawing its structure will be evaluated: 15 and 16. the final exam which relate to compounds containing delocalized electrons, drawing the Lewis structure of resonance contributors (including formal charges) and predicting their relative stabilities will be evaluated: 19 and 20. 7
Given a representation of a set of molecular orbitals for an organic compound with delocalized electrons, rank them according to their potential energy and correctly choose the HOMO (highest occupied molecular orbital) and the LUMO (lowest occupied molecular orbital). Draw the structures for the electrophylic addition products to conjugated dienes and correctly denote the thermodynamic or kinetic product. the final exam which relate to drawing the structures for the electrophylic addition products to conjugated dienes and correctly denoting the thermodynamic or kinetic product will be evaluated: 24 and 25 the final exam which relate to Given a representation of a set of molecular orbitals for an organic compound with delocalized electrons, ranking them according to their potential energy and correctly choosing the HOMO (highest occupied molecular orbital) and the LUMO (lowest occupied molecular orbital) will be evaluated: 21 and 22. the final exam which relate to drawing the structures for the electrophylic addition products to conjugated dienes and correctly denoting the thermodynamic or kinetic product will be evaluated: 24 and 25 Depict the steps in the free radical halogenation of an alkane and predict the product distribution. 8
COURSE MATERIALS: Bruice. Organic Chemistry. 6th edition. Prentice Hall Publishing, 2010. CHEM 2423 Lab Manual. Cengage.Publishing. Freeman. Laboratory Notebook. 2nd edition. VHPS, 2001. Safety Goggles or Visorgogs 9