CHM 235 GENERAL ORGANIC CHEMISTRY I

Transcription

1 CHM 235 GENERAL ORGANIC CHEMISTRY I PRESENTED AND APPROVED: AUGUST 9, 2012 EFFECTIVE: FALL

2 Prefix & Number CHM 235 Course Title: General Organic Chemistry I Purpose of this submission: New Change/Updated Retire If this is a change, what is being changed? Update Prefix Course Description (Check all that apply) Title Course Number Format Change Credits Prerequisite Competencies Textbook/Reviewed Competencies-no changes needed Does this course require additional fees? No Yes If so, please explain. Laboratory course that utilizes consumable materials. Is there a similar course in the course bank? No Yes (Please identify) Articulation: Is this course or an equivalent offered at other two and four-year universities in Arizona? No Yes (Identify the college, subject, prefix, number and title: ASU: CHM 233 (3) & CHM 237 (1); NAU: CHM 235 & CHM 235L; UA: CHEM 241A & CHEM 243A Is this course identified as a Writing Across the Curriculum course? No Yes Course Textbook, Materials and Equipment Textbook(s) Current edition Title Author(s) Publisher Title Author(s) Publisher Organic Chemistry Leroy G. Wade Prentice Hall MasteringChemistry -- Standalone Access Card -- for Organic Chemistry Leroy G. Wade Prentice Hall Course Assessments Description of Possible Course Assessments (Essays, multiple choice, etc.) Exams standardized for this course? Midterm Final Other (Please specify): Where can faculty members locate or access the required standardized exams for this course? The instructor may use the following for evaluation as determined appropriate: 1. Homework problems 2. Quizzes and/or exams, including a final exam 3. Lab reports/quizzes/presentations 4. Demonstration of skills in the laboratory 5. Application of the scientific method in the laboratory Laboratory reports are required to assess content knowledge and writing skills to fulfill requirements of Writing Across the Curriculum for this core class. Are exams required by the department? No Yes If Yes, please specify:

3 Student Outcomes: Identify the general education goals for student learning that is a component of this course. Check all that apply: 1. Communicate effectively. a. Read and comprehend at a college level. b. Write effectively in a college setting. 2. Demonstrate effective quantitative reasoning and problem solving skills. Method of Assessment a. Homework, quizzes, midterm exams, and final exam b. Lab reports, scientific reports/presentations Lab experiments, homework, class exercises, quizzes midterm exams, and final exam 3. Demonstrate effective qualitative reasoning skills. Homework, class exercises, quizzes, midterm exams, and final exam. 4. Apply effective methods of inquiry. a. Generate research paper by gathering information from varied sources, analyzing data and organizing information into a coherent structure. b. Employ the scientific method. 5. Demonstrate sensitivity to diversity a. Experience the creative products of humanity. b. Describe alternate historical, cultural, global perspectives. a. Lab reports, scientific reports/presentations b. Lab experiments demonstrating the proper use and handling of lab equipment and a clear understanding of laboratory procedures and safety principles Laboratory projects, scientific reports/presentations individual or group Office of Instruction Use only: CIP Code: ONET Code: Minimum Qualifications:

4 COURSE INFORMATION Initiator: Lale Cilenti Arac, Paul Haberstroh, Farah Farah Date of proposal to Curriculum Sub-Committee: 8/9/2012 Effective Semester/Year Fall 2013 Spring Summer Prefix & Number: CHM 235 Full Title: General Organic Chemistry I Short Title: General Organic Chemistry I Catalog Course Description: Studies the properties and reactions of aliphatic and aromatic organic with emphasis being placed on reaction mechanism, fundamental principles, and modern instrumental methods. SUN Course Number: CHM 2235 Credit Hours: 4 Lecture Hours: 3 Lab Hours: 3 Prerequisite(s) Completion of CHM 152 with a C. Co-requisite(s) CHM 235L Intended Course Goals By the end of the semester, students will be able to: 1. Predict, given the structural formula or name of a large assortment of organic compounds, o the detailed 2-dimensional and 3-dimensional structure of a molecule; o the reaction products arising from treatment with a variety of reagents; o the way in which bonds are made and broken to bring about product formation in these reactions; o the effect of structural alterations on reactivity (rate or position of equilibrium) in these reactions; o the fundamental physical properties of an organic compound. 2. Construct synthetic schemes by which a variety of organic compounds may be prepared from simple, readily available starting materials utilizing critical thinking skills. 3. Deduce the structural formula of a given or unknown organic compound from spectroscopic (IR, MS and NMR) or chemical reactivity data. 4. Perform laboratory experiments individually and in a cooperative setting, communicate results of laboratory work in written and oral formats. 5. Demonstrate an understanding of 2-dimensional and 3-dimensional structure through use of organic drawing software and molecular modeling. 6. Exhibit cooperative work strategies in solving organic chemistry problems. 7. Demonstrate knowledge of sources, uses and issues pertaining to the use of organic compounds

5 in the practical world.

6 Course Competencies and Objectives By the end of the semester, students will be able to: 1. Competency: Demonstrate understanding of the principles of atomic and molecular structure, bonding, and acid-base chemistry via mastery of the following learning objectives: 1.1. Draw and interpret Lewis, condensed, and line-angle structural formulas. Show which atoms bear formal charges Draw resonance forms and use them to predict stabilities Calculate empirical and molecular formulas from elemental compositions Predict relative acidities and basicities based on structure, bonding, and resonance of conjugate acid-base pairs Identify nucleophiles (Lewis bases) and electrophiles (Lewis acids), and write equations for Lewis acid-base reactions. 2. Competency: Visualize the structure and properties of organic molecules via mastery of the following learning objectives: 2.1. Draw the structure of a single bond, a double bond, and a triple bond Predict the hybridization and geometry of the atoms in a molecule Draw a good three-dimensional representation of a given molecule Identify constitutional isomers and stereoisomers Identify polar and nonpolar molecules and predict which ones can engage in hydrogen bonding Predict general trends in the boiling points and solubilities of compounds, based on their size, polarity, and hydrogen-bonding ability Identify the general classes of hydrocarbons and draw structural formulas for examples Identify the classes of compounds containing oxygen or nitrogen, and draw structural formulas for examples. 3. Competency: Describe the structure and stereochemistry of alkanes via mastery of the following learning objectives: 3.1. Explain and predict trends in physical properties of alkanes Correctly name alkanes, cycloalkanes, and bicyclic alkanes Draw the structure and give the molecular formula, when given the name of an alkane Compare the energies of alkane conformations and predict the most stable conformation Compare the energies of cycloalkanes and explain ring strain Identify and draw cis and trans stereoisomers of cycloalkanes Draw accurate cyclohexane conformations, and predict the most stable conformations of substituted cyclohexanes. 4. Competency: Define and distinguish between the kinetics and thermodynamics involved in chemical reactions via mastery of the following learning objectives: 4.1. Explain the mechanism and energetics of the free-radical halogenation of alkanes Predict the products of halogenation of an alkane, based on the selectivity of halogenation Calculate free-energy changes from equilibrium constants Calculate enthalpy changes from bond-dissociation energies Determine the order of a reaction, and suggest a possible mechanism based on its rate equation Use energy diagrams to discuss transition states, activation energies, intermediates, and the rate-determining step of a reaction Explain how to use isotope effects to determine whether a C-H bond is being broken in the rate-determining step of a reaction Use the Hammond postulate to predict whether a transition state will be reactant-like or product-like 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.

7 5. Competency: Discriminate between molecules with subtle stereochemical differences through visualization of their three-dimensional structures via mastery the following learning objectives: 5.1. Classify molecules as chiral or achiral, and identify mirror planes of symmetry Identify chiral carbon atoms and name them using the (R) and (S) nomenclature Calculate specific rotations from polarimetry data Draw all stereoisomers of a given structure Identify enantiomers, diastereomers, and meso compounds Draw correct Fischer projections of chiral carbon atoms Predict the stereochemistry of products of reactions such as substitutions and eliminations on optically active compounds Predict the differences in products of stereospecific reactions of diastereomers. 6. Competency: Exhibit an understanding of the physical properties and reactions of alkyl halides via mastery of the following learning objectives: 6.1. Predict and explain the rearrangement of cations in first-order reactions Predict which substitutions or eliminations will be faster, based on differences in substrate, base/nucleophile, leaving group, or solvent Predict whether a reaction will be first order or second order Predict predominance of substitution or elimination, when possible Use the Saytzeff rule to predict major and minor elimination products Use retrosynthetic analysis to solve multistep synthesis problems with alkyl halides as reagents, intermediates, or products. 7. Competency: Construct an understanding of the physical properties and synthesis of alkenes, via mastery of the following learning objectives: 7.1. Draw and name all alkenes with a given molecular formula Use the E-Z and cis-trans systems to name geometric isomers Use heats of hydrogenation to compare stabilities of alkenes Predict relative stabilities of alkenes and cycloalkenes, based on structure and stereochemistry Predict the products of dehydrohalogenation of alkyl halides, dehalogenation of dibromides, and dehydration of alcohols, including major and minor products Propose logical mechanisms for dehydrohalogenation, dehalogenation, and dehydration reactions Predict and explain the stereochemistry of E2 eliminations to form alkenes Propose effective single-step and multistep syntheses of alkenes. 8. Competency: Exhibit an understanding of the reactions of alkenes, via mastery of the following learning objectives: 8.1. Predict the products of additions, oxidations, reductions, and cleavages of alkenes, including orientation of reaction (regiochemistry) and stereochemistry Propose logical mechanisms to explain the observed products of alkene reactions, including regiochemistry and stereochemistry Use alkenes as starting materials and intermediates in devising one-step and multistep syntheses Choose the better method and explain its advantages when more than one method is usable for a chemical transformation Use clues provided by products of reactions such as ozonolysis to determine the structure of an unknown alkene. 9. Competency: Demonstrate an understanding of the physical properties, synthesis, and reactions of alkynes, via mastery of the following learning objectives: 9.1. Name alkynes and draw the structure from their names Explain why alkynes are more acidic than alkanes and alkenes.

8 9.3. Propose effective single-step and multistep syntheses of alkynes Predict the products of additions, oxidations, reductions, and cleavages of alkynes, including regiochemistry and stereochemistry Use alkynes as starting materials and intermediates in one-step and multistep syntheses Show how the reduction of an alkyne leads to an alkene or alkene derivative with the desired stereochemistry. 10. Competency: Construct an understanding of the physical properties and synthesis of alcohols, diols, and ethers via mastery of the following learning objectives: Draw and name all alcohols with a given molecular formula Use the E-Z and cis-trans systems to name geometric isomers Use heats of hydrogenation to compare stabilities of alkenes Predict relative stabilities of alkenes and cycloalkenes, based on structure and stereochemistry Predict the products of dehydrohalogenation of alkyl halides, dehalogenation of dibromides, and dehydration of alcohols, including major and minor products Propose logical mechanisms for dehydrohalogenation, dehalogenation, and dehydration reactions Predict and explain the stereochemistry of E2 eliminations to form alkenes Propose effective single-step and multistep syntheses of alcohols. 11. Competency: Develop an understanding of the reactions of alcohols via mastery of the following learning objectives: Predict the products of additions, oxidations, reductions, and cleavages, including regiochemistry and stereochemistry Propose logical mechanisms to explain the observed products of reactions of alcohols, including regiochemistry and stereochemistry Use alcohols as starting materials and intermediates in devising one-step and multistep syntheses Choose the better method and explain its advantages when more than one method is usable for a chemical transformation Use clues provided by products of reactions to determine the structure of an unknown alcohol. 12. Competency: Determine the structure of organic compounds with the use of Infrared (IR) Spectroscopy and Mass Spectrometry (MS) via mastery of the following learning objectives: Identify the reliable characteristic peaks, given an IR spectrum Explain why some characteristic peaks are usually strong or weak and why some may be absent Predict the stretching frequencies of common functional groups Identify functional groups from IR spectra Identify conjugated and strained C=O bonds and conjugated and aromatic C=C bonds from their absorptions in the IR spectrum Determine molecular weights from mass spectra Use mass spectra to recognize the presence of Br, C1, I, N, and S atoms, when possible Predict the major ions from fragmentation of alkanes, alkenes, and alcohols Use the fragmentation pattern to determine whether a proposed structure is consistent with the mass spectrum.