EASTERN ARIZONA COLLEGE General Organic Chemistry I Course Design 2015-2016 Course Information Division Science Course Number CHM 235 (SUN# CHM 2235) Title General Organic Chemistry I Credits 4 Developed by Phil McBride Lecture/Lab Ratio 3 Lecture/3 Lab Transfer Status ASU NAU UA CHM 233 (3) & CHM 237 (1) CHM 235L --and-- CHM 235 CHEM 243A --and-- CHEM 241A Activity Course No CIP Code 40.0500 Assessment Mode Pre/Post Test (62 Questions/130 Points) Semester Taught Fall GE Category Lab Science Separate Lab Yes Awareness Course No Intensive Writing Course No Prerequisites CHM 152 Educational Value Students will gain an understanding of the role that organic chemistry plays in their lives, and the role that organic chemistry plays in the agricultural and medical fields. Students learn how to identify problems and work as a team to solve those problems. Students learn how to predict reactions and devise methods to synthesize organic compounds. Students learn to work as part of a cooperative team. Students learn the composition and reactivity of several chemicals that they will encounter in various scientific fields. The students learn about hazardous waste and safety precautions that must be followed when dealing with organic chemicals. Description General principles of organic chemistry with emphasis on reactivity and synthesis. Topics include bonding, structure and properties of organic compounds, stereochemistry, overview of organic reactions, kinetics and thermodynamics, structure, synthesis, and reaction of alkenes, alkynes, and alkyl halides, nucleophilic substitution and elimination reactions, structure determination using Mass Spectrometry, Infrared Spectroscopy, and Nuclear Magnetic Resonance Spectroscopy, aromaticity, and electrophilic aromatic substitution reactions. EASTERN ARIZONA COLLEGE - 1 - General Organic Chemistry I
Supplies Laboratory Notebook: Comp Book 5x5 Ruled Scientific Calculator Competencies and 1. Review the principles of atomic and molecular structure, bonding, and acid-base chemistry. a. Draw and interpret Lewis, condensed, and line-angle structural formulas. Show which atoms bear formal charges. b. Draw resonance forms and use them to predict stabilities. c. Calculate empirical and molecular formulas from elemental compositions. d. Predict relative acidities and basicities based on structure, bonding, and resonance of conjugate acid-base pairs. e. Identify nucleophiles (Lewis bases) and electrophiles (Lewis acids), and write equations for Lewis acid-base reactions. 2. Visualize the structure and properties of Organic Molecules. a. Draw the structure of a single bond, a double bond, and a triple bond. b. Predict the hybridization and geometry of the atoms in a molecule. c. Draw a good three-dimensional representation of a given molecule. d. Identify constitutional isomers and stereoisomers. e. Identify polar and nonpolar molecules and predict which ones can engage in hydrogen bonding. f. Predict general trends in the boiling points and solubilities of compounds, based on their size, polarity, and hydrogen-bonding ability. g. Identify the general classes of hydrocarbons and draw structural formulas for examples. h. Identify the classes of compounds containing oxygen or nitrogen, and draw structural formulas for examples. EASTERN ARIZONA COLLEGE - 2 - General Organic Chemistry I
3. Acquaint self with the structure and stereochemistry of Alkanes. a. Explain and predict trends in physical properties of alkanes. b. Correctly name alkanes, cycloalkanes, and bicyclic alkanes. c. Draw the structure and give the molecular formula, when given the name of an alkane. d. Compare the energies of alkane conformations and predict the most stable conformation. e. Compare the energies of cycloalkanes and explain ring strain. f. Identify and draw cis and trans stereoisomers of cycloalkanes. g. Draw accurate cyclohexane conformations, and predict the most stable conformations of substituted cyclohexanes. 4. Develop an understanding of the kinetics and thermodynamics involved in chemical reactions. a. Explain the mechanism and energetics of the free-radical halogenation of alkanes. b. Predict the products of halogenation of an alkane, based on the selectivity of halogenation. c. Calculate free-energy changes from equilibrium constants. d. Calculate enthalpy changes from bond-dissociation energies. e. Determine the order of a reaction, and suggest a possible mechanism based on its rate equation. f. Use energy diagrams to discuss transition states, activation energies, intermediates, and the rate-determining step of a reaction. g. Explain how to use isotope effects to determine whether a C-H bond is being broken in the rate-determining step of a reaction. h. Use the Hammond postulate to predict whether a transition state will be reactant-like or EASTERN ARIZONA COLLEGE - 3 - General Organic Chemistry I
product-like. i. Describe the structures of carbocations, carbanions, free radicals, and carbenes and the structural features that stabilize them. Explain which are electrophilic and which are nucleophilic. 5. Visualize the three-dimensional structure of molecules in order to discriminate between molecules with subtle stereochemical differences. a. Classify molecules as chiral or achiral, and identify mirror planes of symmetry. b. Identify chiral carbon atoms and name them using the (R) and (S) nomenclature. c. Calculate specific rotations from polarimetry data. d. Draw all stereoisomers of a given structure. e. Identify enantiomers, diastereomers, and meso compounds. f. Draw correct Fischer projections of chiral carbon atoms. g. Predict the stereochemistry of products of reactions such as substitutions and eliminations on optically active compounds. h. Predict the differences in products of stereospecific reactions of diastereomers. 6. Develop an understanding of the physical properties and reactions of alkyl halides. a. Predict and explain the rearrangement of cations in first-order reactions. b. Predict which substitutions or eliminations will be faster, based on differences in substrate, base/nucleophile, leaving group, or solvent. c. Predict whether a reaction will be first order or second order. d. Predict predominance of substitution or elimination, when possible. EASTERN ARIZONA COLLEGE - 4 - General Organic Chemistry I
e. Use the Saytzeff rule to predict major and minor elimination products. f. Use retrosynthetic analysis to solve multistep synthesis problems with alkyl halides as reagents, intermediates, or products. 7. Construct an understanding of the physical properties and synthesis of alkenes. a. Draw and name all alkenes with a given molecular formula. b. Use the E-Z and cis-trans systems to name geometric isomers. c. Use heats of hydrogenation to compare stabilities of alkenes. d. Predict relative stabilities of alkenes and cycloalkenes, based on structure and stereochemistry. e. Predict the products of dehydrohalogenation of alkyl halides, dehalogenation of dibromides, and dehydration of alcohols, including major and minor products. f. Propose logical mechanisms for dehydrohalogenation, dehalogenation, and dehydration reactions. g. Predict and explain the stereochemistry of E2 eliminations to form alkenes. h. Propose effective single-step and multistep syntheses of alkenes. 8. Develop an understanding of the reactions of alkenes. a. Predict the products of additions, oxidations, reductions, and cleavages of alkenes, including (a) Orientation of reaction (regiochemistry) (b) Stereochemistry. b. Propose logical mechanisms to explain the observed products of alkene reactions, including regiochemistry and stereochemistry. c. Use alkenes as starting materials and intermediates in devising one-step and multistep EASTERN ARIZONA COLLEGE - 5 - General Organic Chemistry I
syntheses. d. Choose the better method and explain its advantages when more than one method is usable for a chemical transformation. e. Use clues provided by products of reactions such as ozonolysis to determine the structure of an unknown alkene. 9. Develop an understanding of the physical properties, synthesis, and reactions of alkynes a. Name alkynes and draw the structure from their names. b. Explain why alkynes are more acidic than alkanes and alkenes. Show how to generate nucleophilic acetylide ions and heavy-metal acetylides. c. Propose effective single-step and multistep syntheses of alkynes. d. Predict the products of additions, oxidations, reductions, and cleavages of alkynes, including orientation of reaction (regiochemistry) and stereochemistry. e. Use alkynes as starting materials and intermediates in one-step and multistep syntheses. f. Show how the reduction of an alkyne leads to an alkene or alkene derivative with the desired stereochemistry. 10. Determine the structure of organic compounds with the use of Infrared (IR) Spectroscopy and Mass Spectrometry (MS). a. Given an IR spectrum, identify the reliable characteristic peaks. b. Explain why some characteristic peaks are usually strong or weak and why some may be absent. EASTERN ARIZONA COLLEGE - 6 - General Organic Chemistry I
c. Predict the stretching frequencies of common functional groups. d. Identify functional groups from IR spectra. e. Identify conjugated and strained C=O bonds and conjugated and aromatic C=C bonds from their absorptions in the IR spectrum. f. Determine molecular weights from mass spectra. g. Use mass spectra to recognize the presence of Br, C1, I, N, and S atoms, when possible. h. Predict the major ions from fragmentation of alkanes, alkenes, and alcohols. i. Use the fragmentation pattern to determine whether a proposed structure is consistent with the mass spectrum. 11. Determine the structure of organic compounds with the use of Nuclear Magnetic Resonance Spectroscopy (NMR). a. Given a structure, determine which protons are equivalent and which are nonequivalent; predict the number of signals and their approximate chemical shifts. b. Use the integral trace to determine the relative numbers of different types of protons. c. Predict which protons in a structure will be magnetically coupled, and predict the number of peaks. d. Use proton spin-spin splitting patterns to determine the structure of alkyl and other groups. e. Draw the general features of the NMR spectrum of a given compound. f. Predict the approximate chemical shifts of carbon atoms in a given compound. g. Combine information from NMR, IR, and MS spectra to determine the structures of organic compounds. o EASTERN ARIZONA COLLEGE - 7 - General Organic Chemistry I
12. Consider the unique properties of conjugated systems and methods used to detect them (UV spectroscopy) a. Show how to construct the molecular orbitals of ethylene, butadiene, and the allylic system. b. Show the electronic configurations of ethylene, butadiene, and the allyl cation, radical, anion. c. Recognize reactions that are enhanced by resonance stabilization of the intermediates. d. Develop mechanisms to explain the enhanced rates of observed products. e. Predict the products of Diels-Alder reactions. 13. Visualize the structure and properties of aromatic compounds. a. Construct the molecular orbitals of a cyclic system of p orbitals similar to benzene and cyclobutadiene. b. Use the polygon rule to draw the energy diagram for a cyclic system of p orbitals, and fill in the electrons to show whether a given compound or ion is aromatic or antiaromatic. c. Use Huckel's rule to predict whether a given annulene, heterocycle, or ion will be aromatic, antiaromatic, or nonaromatic. d. Name aromatic compounds and draw their structures from the names. e. Use IR, NMR, UV, and mass spectra to determine the structures of aromatic compounds. f. Given an aromatic compound, predict the important features of its spectra. EASTERN ARIZONA COLLEGE - 8 - General Organic Chemistry I
14. Demonstrate the reactions of aromatic compounds. a. Predict products and give mechanisms for the common electrophilic aromatic substitutions: halogenation, nitration, sulfonation, and Friedel-Crafts alkylation and acylation. b. Draw resonance structures for the sigma complexes resulting from electrophilic attack on substituted aromatic rings. c. Predict the position(s) of electrophilic aromatic substitution on molecules containing substituents on one or more aromatic rings. d. Design syntheses that use the influence of substituents to generate the correct isomers of multisubstituted aromatic compounds. e. Predict the products of Birch reduction, hydrogenation, and chlorination of aromatic compounds. Types of Instruction Classroom Lecture Discussion Cooperative Learning Activities Multi-Media Presentations Laboratory Activities Grading Information Grading Rationale Exams will be given after every 2 or 3 chapters in the textbook. Laboratory activities will be held each week. Laboratory notebooks will be turned in and graded each week. A post test will be given at the end of the semester. Category Weights Pre-test: 0% Homework: 15% Laboratory activities: 25% Exams: 50% Post Test: 10% EASTERN ARIZONA COLLEGE - 9 - General Organic Chemistry I
Grading Scale A 90-100% B 80-89% C 65-79% D 50-64% F 0-59% EASTERN ARIZONA COLLEGE - 10 - General Organic Chemistry I