| |
Close Window/Tab
PRINT VIEW -- Opens in new, second window. Use browser controls to close when finished.
| Credit- Degree applicable | | Effective Quarter: Fall 2021 | I. Catalog Information
| CHEM 12B | Organic Chemistry | 5 Unit(s) |
| | Requisites: Prerequisite: CHEM 12A with a grade of C or better.
Advisory: EWRT 1A or EWRT 1AH or (EWRT 1AS and EWRT 1AT) or ESL 5. Hours: Lec Hrs: 36.00
Lab Hrs: 72.00
Out of Class Hrs: 72.00
Total Student Learning Hrs: 180.00 Description: An exploration of the physical properties and chemical behavior of important classes of organic compounds, focusing on: alkynes, polyenes; aromatic compounds; alcohols, thiols, and ethers; and aldehydes and ketones and their derivatives. Emphasis on retrosynthesis, spectroscopic structure determination, and reaction mechanism. Laboratory experiments involving the synthesis of simple compounds and the characterization of those compounds using chromatography and infrared (IR), ultraviolet-visible (UV-Vis), and nuclear magnetic resonance (NMR) spectroscopy. For chemistry majors or those in closely-allied fields such as biochemistry and chemical engineering. |
| Student Learning Outcome Statements (SLO)
| | | • Student Learning Outcome: Construct logical multi-step syntheses for organic molecules |
| | | • Student Learning Outcome: Use Molecular Orbital theory and Resonance to explain reactions of benzene and other molecules with conjugated π systems |
| | | • Student Learning Outcome: Increase breadth of knowledge of organic reactions to include functional groups containing oxygen, benzene and more complex π systems |
| | | • Student Learning Outcome: Construct molecular structures of increasingly complex molecules from IR, 1H NMR, and 13C NMR data |
|
II. Course Objectives | A. | Examine the key structural features and physical properties of important classes of organic compounds, especially: alkynes; polyenes; aromatic compounds; alcohols, phenols, and ethers; thiols and sulfides; aldehydes and ketones; acetals and ketals; and imines and enamines. |
| B. | Compose valid names for alkynes, alcohols, ethers, thiols, aldehydes, ketones, benzene and its derivatives, and related organic compounds using both common and IUPAC nomenclature conventions. |
| C. | Predict the reactivity of alkynes, aldehydes, alcohols, ethers, thiols, aldehydes, ketones, benzene and its derivatives, and related organic compounds on the basis of their structure. |
| D. | Create detailed reaction mechanisms and use those mechanisms to explain experimental observations or predict the most likely outcome of reactions of alcohols, alkynes, ethers, thiols, aldehydes, ketones, benzene and its derivatives, and related organic compounds. |
| E. | Construct detailed synthetic schemes for the interconversion of alkynes, alcohols, ethers, thiols, aldehydes, ketones, benzene and its derivatives, and related organic compounds by functional group transformation using retrosynthetic analysis. |
| F. | Examine the behavior of alcohols, alkynes, ethers, thiols, aldehydes, ketones, benzene and its derivatives, and related organic compounds by utilizing the frameworks of kinetics, thermodynamics, and equilibrium. |
III. Essential Student Materials | | Safety Goggles
Combination Lock |
IV. Essential College Facilities | | Fully equipped chemical laboratory including, at a minimum, the following: consumable chemicals, chemical balances, nitrile gloves, hotplates, glassware, melting point apparatus, fume hoods, chemical disposal facilities, lockable student storage areas, and a laboratory support technician. Additionally, access to analytical equipment including IR and NMR spectrometers and Gas Chromatographs along with associated interpretation software is required |
V. Expanded Description: Content and Form | A. | Examine the key structural features and physical properties of important classes of organic compounds, especially: alkynes; polyenes; aromatic compounds; alcohols, phenols, and ethers; thiols and sulfides; aldehydes and ketones; acetals and ketals; and imines and enamines. |
| 1. | Examine the effects of conjugation on molecular structure and electronic structure. |
| 2. | Compare the reactivity of aldehydes and ketones |
| B. | Compose valid names for alkynes, alcohols, ethers, thiols, aldehydes, ketones, benzene and its derivatives, and related organic compounds using both common and IUPAC nomenclature conventions. |
| 1. | Examine the guidelines for naming compounds based on current IUPAC committee recommendations for organic compounds. |
| b. | Alcohols, thiols, and ethers |
| 2. | Survey key examples of traditional or common nomenclature. |
| a. | Common names of aldehydes and ketones, such as acetone and methyl ethyl ketone (MEK) |
| b. | Common names of aromatic compounds, such as xylene, styrene, toluene, phenol, aniline, cumene, and acetophenone |
| C. | Predict the reactivity of alkynes, aldehydes, alcohols, ethers, thiols, aldehydes, ketones, benzene and its derivatives, and related organic compounds on the basis of their structure. |
| 1. | Investigate the influence of delocalization on the reactivity of polyenes and other linearly conjugated systems. |
| 1. | Conjugated versus unconjugated polyenes |
| 1. | Writing resonance structures |
| 2. | Blending of resonance forms to more accurately represent molecular structure |
| c. | Molecular orbitals in conjugated systems |
| 1. | Generation of delocalized molecular orbitals through combination of atomic orbitals |
| 2. | Bonding, non-bondings, and anti-bonding orbitals |
| 2. | Assess the relationship between structure and reactivity in pericyclic reactions |
| a. | Determination of frontier (HOMO/LUMO) orbital geometry |
| b. | Conrotatory versus disrotatory cyclization geometries |
| c. | Suprafacial versus antarafacial addition |
| d. | Thermal versus photochemical reactions |
| e. | The Diels-Alder reaction |
| 3. | Examine the effects of aromaticity on chemical reactivity. |
| 1. | Observation of aromaticity through heats of hydrogenation |
| 2. | Structural effects of aromaticity on bond length and strength |
| 3. | Resonance structures of aromatic compounds |
| 1. | Structural prerequisites for aromaticity |
| 2. | Molecular orbital explanation for the Huckel [4n + 2] rule |
| 3. | Aromatic stabilization and anti-aromatic destabilization of cyclic molecules |
| 5. | Effects of antiaromaticity on molecular structure, such as the non-planarity of cyclooctatetraene and the thermodynamic instability of cyclobutadiene |
| 4. | Estimate the acidity of organic molecules. |
| b. | Acidity of aromatic compounds |
| 1. | Resonance stabilization of benzoate |
| 2. | Resonance stabilization of phenoxide |
| D. | Create detailed reaction mechanisms and use those mechanisms to explain experimental observations or predict the most likely outcome of reactions of alcohols, alkynes, ethers, thiols, aldehydes, ketones, benzene and its derivatives, and related organic compounds. |
| 1. | Examine the effects of delocalization on reaction mechanism. |
| a. | Conjugate (1,4) versus vicinal (1,2) addition |
| b. | Electrophilic aromatic substitution versus electrophilic addition to alkenes |
| 2. | Explore the major reactions of aromatic compounds. |
| a. | Electrophilic aromatic substitution |
| b. | Friedel-Crafts alkylation |
| c. | Friedel-Crafts acylation |
| d. | Nucleophlic aromatic substitution |
| 1. | Stability of benzene towards catalytic hydrogenation |
| 2. | Reduction of nitro groups |
| 3. | Investigate the reactions of alcohols, thiols, and ethers. |
| a. | Dehydration of alcohols |
| b. | Conversion of alcohols into leaving groups |
| 3. | Tosyl chloride and related sulfonyl halides |
| 4. | Stereochemical consequences of leaving group formation |
| 2. | Pyridinium chlorochromate (PCC) |
| d. | Epoxide formation and reaction |
| 1. | Formation of epoxides from alkenes using peroxyacids |
| 2. | Epoxidation via elimination of halohydrins |
| 3. | Acid-catalyzed ring-opening |
| 4. | Base-promoted ring-opening |
| e. | Protecting groups for alcohols |
| 1. | Protecting group synthetic stratagy |
| 2. | Trimethysilyl (TMS) ethers and related silyl ethers |
| 3. | Tetrahydropyran (THP) ethers |
| 4. | Benzyl ethers (optional) |
| 5. | Deprotection conditions |
| 4. | Survey the major reactions of aldehydes and ketones. |
| a. | Reactivity of the carbonyl bond |
| 1. | Electrophilicity of carbon |
| 2. | Cationic versus anionic reactions and mechanisms |
| b. | Hydrates, acetals, and ketals |
| 2. | Use of acetals and ketals as protecting groups |
| c. | Formation of imines, enamines, hydrazones, and oximes |
| 1. | Over-oxidation of hydrates of aldehydes |
| 1. | Sodium borohydride and lithium aluminum hydride |
| 1. | Formation and reaction of Grignard reagents |
| 2. | Conjugate addition of organocuprates |
| 3. | Functional group compatibility |
| h. | Cannizzaro reaction and relationship to NADH mechanism (optional) |
| 5. | Explore the major reactions of alkynes. |
| 2. | Keto-enol tautomerization |
| 2. | Tautomerization of the intermediate formed during oxidation of an alkenylborane |
| 1. | Exhaustive hydrogenation (H2/Pt) |
| 3. | Sodium/ammonia reduction |
| 1. | Relative acidity of the acetylenic proton |
| 2. | Limitation to primary haloalkanes and related substrates |
| E. | Construct detailed synthetic schemes for the interconversion of alkynes, alcohols, ethers, thiols, aldehydes, ketones, benzene and its derivatives, and related organic compounds by functional group transformation using retrosynthetic analysis. |
| 1. | Evaluate the utility of Grignard and Wittig reactions in the synthesis of larger molecules by the formation of new carbon-carbon bonds. |
| 2. | Explore the use of alcohols as key synthetic intermediates. |
| 3. | Investigate the use of oxidation and reduction reactions in multistep synthesis. |
| F. | Examine the behavior of alcohols, alkynes, ethers, thiols, aldehydes, ketones, benzene and its derivatives, and related organic compounds by utilizing the frameworks of kinetics, thermodynamics, and equilibrium. |
| 1. | Contrast kinetic versus thermodynamic control in chemical reactions. |
| a. | Reaction coordinate diagrams of systems experiencing kinetic versus thermodynamic control |
| b. | Effects of temperature on product distribution |
| 2. | Predict the reactivity of aromatic compounds in electrophilic substitution reactions |
| 1. | Resonance stabilization of reaction intermediate |
| 2. | Activators versus deactivators |
| 1. | Avoidance of resonance destabilization |
| 3. | Investigate the reversibility of reactions involving carbonyl-containing compounds |
| a. | Reversibility of cationic (acid-catalyzed) reactions |
| b. | Irreversibility of anionic (base-promoted) reactions |
| c. | Keto-enol tautomerization |
| 1. | Relative stability of ketones versus enols |
| 2. | Relative stability of imines versus enamines |
VI. Assignments | A. | Required readings from the textbook and laboratory manual |
| B. | Discretionary written problems from each lecture chapter and laboratory experiment |
| C. | Written laboratory reports for each experiment performed |
| D. | Periodic quizzes and mid-term examinations based on material discussed in lectures and/or reading assignments |
VII. Methods of Instruction | | Lecture and visual aids
Laboratory demonstrations
Discussion of assigned readings
Discussion of problem solving performed in class
Quiz and examination review performed in class
Homework assignments
Collaborative learning and small group exercises
Laboratory experience which involves students in formal exercises of data collection and analysis
Laboratory discussion sessions and quizzes that evaluate the experiments performed |
VIII. Methods of Evaluating Objectives | A. | At least three written examinations designed to periodically assess the students' ability to apply concepts and skills acquired through one of more modes of instruction, such as lecture, assigned readings, small group discussions, or homework problems. |
| B. | Regular homework assignments and/or lecture quizzes designed to periodically assess the students' progress in acquiring key concepts and skills. |
| C. | Laboratory reports for each experiment performed, which will be used to assess the ability of a student to clearly and logically express the qualitative or quantitative results of an experiment. Laboratory reports will include an analysis of any relevant spectral or physical data and a discussion of theoretical or experimental concepts applied in the experiment. |
| D. | Comprehensive final lecture exam designed to assess the students' ability to critically apply concepts and skills introduced throughout the course. |
| E. | One-hour written and/or practical laboratory final examination designed to assess the students' ability to apply concepts and skills acquired through conducting laboratory experiments and preparing written laboratory reports. |
IX. Texts and Supporting References | A. | Examples of Primary Texts and References |
| 1. | *Klein, David. "Organic Chemistry," 3e with Enhanced Student Solutions Manual and Study Guide. Wiley, 2017 |
| 2. | *Gilbert, John C. and Martin, Stephen F. "Experimental Organic Chemistry: A Miniscale and Microscale Approach", 6e. Brooks/Cole, 2015. |
| B. | Examples of Supporting Texts and References |
X. Lab Topics | 1. | Maintaining a laboratory notebook |
| 2. | Writing laboratory reports |
| 1. | Safety data sheets (SDS) |
| a. | Separation of waste streams |
| b. | Proper disposal methods |
| c. | Environmental hazards of improper waste disposal |
| a. | Maintaining laboratory cleanliness |
| c. | Segregation of chemicals by hazard |
| b. | Limiting chemical exposure |
| e. | Proper use of fire extinguishers |
| C. | Analyze spectroscopic data to determine the structure of organic compounds. |
| 1. | Review the central concepts of spectroscopy. |
| 2. | Analyze organic compounds using infrared (IR) spectrophotometry. |
| a. | Effects of conjugation on bond stretching |
| b. | Interpretation of IR spectra |
| 3. | Analyze organic compounds using ultraviolet-visible (UV) spectrophotometry. |
| a. | Electronic energy levels and absorption of UV-Vis em radiation |
| b. | Color and extended conjugation |
| 4. | Elucidate the structure of organic compounds using nuclear magnetic resonance spectroscopy (NMR). |
| a. | Deshielding effects of aromatic compounds |
| b. | Interpretation of NMR spectra |
| 5. | Analyze compounds using mass spectroscopy (MS) |
| b. | Features of mass spectra useful in structure elucidation |
| c. | Fragmenting patterns and stability of radical cations |
| d. | The molecular ion peak and molar mass |
| e. | Isotopic abundance and M+1 or M+2 signals |
| 1. | Investigation of kinetic versus thermodynamic control of product distribution in chemical reactions, such as the competing synthesis of two semicarbazones |
| 2. | Synthesis of an alkene via a Diels-Alder reaction |
| 3. | Investigation of the reactivity of aromatic compounds via bromonation |
| 4. | Friedel-Crafts acylation of aromatic compounds |
| 5. | Synthesis of an alcohol such as triphenylmethanol via Grignard alkylation |
| 6. | Oxidation of an alcohol such as cyclododecanol |
| 7. | Reduction of a ketone or aldehyde such as camphor |
| 8. | Synthesis of an alkene via Wittig reaction |
|
