PRIOR SYLLABUS. SUBJECT TO CHANGE. CONTACT INSTRUCTOR FOR FURTHER QUESTIONS.
CHEM 141 Summer 2008 Instructor: Dr. David E. Horn Lecture: 9-12 am Lab: MTW 1-4 pm Office: 237A Office Hours: MTWF 12-1 or by appointment Required Texts: ORGANIC CHEMISTRY, McMurry 7th Ed. Recommended Texts: STUDY GUIDE AND SOLUTIONS MANUAL to accompany the 7th Edition of McMurry MULTIPLE CHOICE PROBLEMS IN ORGANIC CHEMISTRY, Horn and Leonard The lecture component of your course grade will be determined as follows: Daily Quizzes………… Exam 1 Friday, June 13 Exam II Friday, June 20 Exam III Friday, June 27 Final Exam – Thurs. July, 3 Final = 2 –15 point units Drop one 15 point unit TOTAL CLASSROOM POINTS = Laboratory TOTAL 141 POINTS 15 points 15 points 15 points 15 points 30 points
75 25 points 100 Points
Exams and classes begin at 9 am. Please bring a watch to all exams. Please do NOT bring activated cell phones, pager, iPods, etc to class or exams. There IS class starting at 10:45 after each hour exam.
Please address questions on exams or quizzes within 48 hours of the return of the graded work. Specific problem assignments are on a separate sheet.
CHEM 141 Summer 2008 Dr. Horn Chapter 1 in McMurry Assigned Problems 1-7 8-13 14 15-17 22,24,26, 28,29,30 Others TBA
Topic Atomic Structure and Electron Configurations Bonding Theory (Valence Bond Theory Hybrid Orbitals (Methane, Ethane, Ethene, & Ethyne Hybridization of N, O, P, and S Drawing Chemical Structures Miscellaneous Problems
Chapter 2 – Polar Covalent Bonds: Acids and Bases Electronegativity, Dipole Moments & Formal Charges Resonance, Resonance Forms and Structure Drawing Acids and Bases: Definitions- Bronsted-Lowry Acid-Bases Strengths Predicting Acid-Based Strength from pKa Values Organic Acids and Bases Curved Arrows and the Lewis Theory Molecular Models Noncovalent Interactions-Solubilities Chapter 3 – Alkanes and Their Stereochemistry Functional Groups Alkanes and Alkane Isomers Alkyl Groups Naming Alkanes Properties of Alkanes Conformations of Ethane Conformations of OtherAlkanes
1-9 10 11 12,13 14-16 17-18 19
1-3 4-6 7-10 11-14
15,16,20 Others TBA
Chapter 4 – Cycloalkanes and their Stererochemistry Naming Cycloalkanes Cis-Trans Isomerism in Cycloalkanes Stability of Cycloalkanes – Ring Strain Conformations of Cycloalkanes Conformations of Cyclohexane Axial and Equatorial Bonds in Cyclohexane Conformations of Monosubstituted Cyclohexanes Conformations of Disubstituted Cyclohexanes Conformations of Polycyclic Molecules Additional Special Topic Chapter 5 – An Overview of Organic Reactions Kinds of Organic Reactions How Organic Reactions Occur: Mechanisms Radical Reactions Polar Reactions, An Example A Mechanism of a Polar Reaction Using Curved Arrows Describing a Reaction: Equilibrium, Rates and Energy Changes Bond Dissociation Energies Energy Diagrams and Transition States Intermediates Biological Reactions vs. Laboratory Reactions Additional Problems Chapter 6 – Alkenes: Structure and Reactivity Industrial Prep and Use Calculating Degree of Unsaturation Naming Alkenes Cis-Trans Isomerism Sequence Rules: E vs Z Alkene Stability Electrophilic Addition Reactions of Alkenes Markovnikov’s Rule Carbocation Stability and Structure
1-3 4,6 9
12-14 16 19 28,36,39,48,53
1 2,3 4,5, 6-9 10,11 12
1-3 4,5,6 7,8b 9,10,11 13 14,15 16
Chapter 6 – Continued The Hammond Postulate Carbocation Rearrangements Additional Problems
Problems 19 23,24,29,48,49
Chapter 7 – Alkenes: Reactions and Synthesis Preparation of Alkenes: A preview of Elimination Rxns 1&2 Addition of Halogens 3&4 Addition of Hypohalous Acids 5&6 Addition of Water:Oxymercuration-Demercuration 7,8 Addition of Water: Hydroboration 9,10 Addition of Carbenes 12 Addition of Hydrogen (Hydrogenation) 13 Epoxidation and Hydroxylation 14,15 Cleavage to Carbonyl Compounds 16,17 Radical Addition – Polymerization 18,19 Biological Additions of Radicals to Alkenes Additional Problems 24,26,26,56 Chapter 8 – Alkynes: An Introduction to Organic Synthesis Naming Alkynes Preparing Alkynes Reacting Alkynes Addition of HX and X2 Hydration Oxidative Cleavage of Alkynes Alkyne Acidity Alkylation of Acetylide ions Intoduction to Organic Synthsis Additional Problems Chapter 9 – Stereochemistry Enantiomers and the Tetrahedral Carbon Chirality Optical Activity 1,2
4,5 6,7,8 9 10,11 12 a,e,f 13 a,c TBA
Pasteur’s Discovery of Enantiomers Sequence Rules for Specifying Configurations Diastereromers Meso Compounds Resolution of Racemic Mixtures Review of Isomerism Stereochemistry of Reactions: Addition of Water to An Achiral Alkene Stereochemistry of Reactions: Addition of Water to a Chiral Alkene Chirality of Nitrogen, Phosphorus, and Sulfur Prochirality Chiral Drugs. Additional Problems Chapter 10 – Organohalides Naming Alkyl Halides Structures Preparing Alkyl Halides from Alkanes Preparing Alkyl Halides from Alkenes (Allylic Bromination) Allyl Radical Stability Preparing Alkyl Halides from Alcohols Reactions of Alkyl Halides to make Grignards Organocoupling Reactions Oxidation and Reduction in Organic Chemistry Additional Problems
7,8,9,11 12,13 14,16 18 20
1,2 3,4 5,6,7
8 9,10 11 12,13 TBA