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General Organic Chemistry I Course Design 2021-2022 EASTERN ARIZONA COLLEGE General Organic Chemistry I Course Design 2021-2022 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 CHM 235 --and-- CHEM 243A --and-- 237 (1) CHM 235L CHEM 241A Activity Course No CIP Code 40.0500 Assessment Mode Standardized Test (ACS Organic Chemistry Form 2017 - 70 Questions/70 Points) Semester Taught Fall GE Category Lab Science Separate Lab Yes Awareness Course No Intensive Writing Course No Diversity and Inclusion 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 Equal Opportunity Employer and Educator Supplies Laboratory Notebook: Comp Book 5x5 Ruled Scientific Calculator Competencies and Performance Standards 1. Draw valid atomic and molecular structures, describe bonding, and apply acid-base chemistry in the solving of problems. Learning objectives What you will learn as you master the competency: 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. Performance Standards Competence will be demonstrated: o through completion of a weekly laboratory report o through successful completion of periodic written examinations Criteria - Performance will be satisfactory when: o learner completes assigned homework at 80% or higher o learner participates in active learning activities o learner completes stipulated laboratory activities o learner successfully passes exams covering competencies 2. Draw valid structures and predict properties of organic molecules. Learning objectives What you will learn as you master the competency: 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 solubility 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 Equal Opportunity Employer and Educator Performance Standards Competence will be demonstrated: o through completion of a weekly laboratory report o through successful completion of periodic written examinations Criteria - Performance will be satisfactory when: o learner completes assigned homework at 80% or higher o learner participates in active learning activities o learner completes stipulated laboratory activities o learner successfully passes exams covering competencies 3. Draw the structure and identify the stereochemistry of basic alkanes. Learning objectives What you will learn as you master the competency: 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. Performance Standards Competence will be demonstrated: o through completion of a weekly laboratory report o through successful completion of periodic written examinations Criteria - Performance will be satisfactory when: o learner completes assigned homework at 80% or higher o learner participates in active learning activities o learner completes stipulated laboratory activities o learner successfully passes exams covering competencies 4. Apply the concepts of kinetics and thermodynamics to describe mechanisms. Learning objectives What you will learn as you master the competency: 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. EASTERN ARIZONA COLLEGE - 3 - General Organic Chemistry I Equal Opportunity Employer and Educator 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 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. Performance Standards Competence will be demonstrated: o through completion of a weekly laboratory report o through successful completion of periodic written examinations Criteria - Performance will be satisfactory when: o learner completes assigned homework at 80% or higher o learner participates in active learning activities o learner completes stipulated laboratory activities o learner successfully passes exams covering competencies 5. Use three-dimensional structures of molecules to discriminate between molecules with subtle stereochemical differences. Learning objectives What you will learn as you master the competency: 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. Performance Standards Competence will be demonstrated: o through completion of a weekly laboratory report o through successful completion of periodic written examinations Criteria - Performance will be satisfactory when: o learner completes assigned homework at 80% or higher o learner participates in active learning activities o learner completes stipulated laboratory activities o learner successfully passes exams covering competencies EASTERN ARIZONA COLLEGE - 4 - General Organic Chemistry I Equal Opportunity Employer and Educator 6. Describe the physical properties and predict basic reactions of alkyl halides. Learning objectives What you will learn as you master the competency: 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. 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. Performance Standards Competence will be demonstrated: o through completion of a weekly laboratory report o through successful completion of periodic written examinations Criteria
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