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ChemWiki i-clicker Organic Questions

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  • Eight-point checklist for participating in the ChemWiki Extra Credit Project

    1. Please refer to the topics list below. Consider a ChemWiki set of 5-10 i-clicker questions (5 minimum), for those topics highlighted in red (one or more questions for each is acceptable, but no more than 2 per topic). Refer to the Chem 227 in-class Powerpoint slides and embedded i-clicker questions from the course calendar for some ideas. However, your questions MUST be unique. They may be similar, but not the same as those previously used in class. Also, refer to  the Organic Chemwiki or Dr. Reusch's, Virtual Textbook of Organic Chemistry, and then select one or more topics that have not been yet chosen from the following list. Including structures in the questions is much preferred than text only.
    2. Register for an account online via the upper right hand corner of the ChemWiki's front page.
    3. Sign up for the ChemWiki Topics at the bottom of this page. (Enter your name in the table and refer to.)
    4. Pages will not need be constructed.
    5. If you complete all 3 phases ( it must be for 5 questions), you will be eligible for 40 raw points (~ equal to the value of 1 lab or 1 1/2 quizzes) which will be added to your total points (quizzes, exams, labs) before i-clicker and Webassign additions.
    6. You will be given credit for anything submitted by noon May 28 on a pro rata basis (40 total pts scaled) for questions. (10 Questions Phase I (max 2 per topic) that are of very high quality and with structures will be given the highest consideration.)
    7. Questions must be in Word format and files e-mailed to Dr. R as attachments ( by noon Friday May 28th to be considered.
    8. All extra credit awards are non-negotiable and final.

    Consider  ChemWiki questions for those topics below that are highlighted in red or brown by clicking "Edit Page" and then typing your name next to the topic you desire below (see example for me below).  No erasing other students' names. Links will be added to your question afterwards if not existing now. Suggestions for other topics are accepted.


    Question(s) Topic Name (Phase I)
    Select only ONE Topic
    Name (Phase II)
    Max of TWO people per Question Topic

    Name (Phase III)
    Select ONE Question Topic from Phase II

    Unit II: Arenes and Aromaticity

     Arenes and Aromaticity    
    Kekulé and the Structure of Benzene      
    A Resonance Picture of Bonding in Benzene  Sehwan Oh    
    The Stability of Benzene  Anh Do    
    An Orbital Hybridization View of Bonding in Benzene  Tina Lee    
    The Pi Molecular Orbitals of Benzene  Sehwan Oh    
    Substituted Derivatives of Benzene and Their Nomenclature  Euna Kim    
    Polycyclic Aromatic Hydrocarbons      
    Physical Properties of Arenes      
    Carbon Clusters, Fullerenes, and Nanotubes      
    Reactions of Arenes: A Preview      
    The Birch Reduction  Eriko Iseki    
    Free-Radical Halogenation of Alkylbenzenes  Tina Lee    
    Oxidation of Alkylbenzenes  Taehoon Ji, Shierly Mayasari     
    Sn1 Reactions of Benzylic Halides  Andrew Kim    
    Sn2 Reactions of Benzylic Halides  Tuba Nemati    
    Addition Reactions of Alkenylbenzenes  Monib Hai    
    Polymerization of Styrene      
    Cyclobutadiene and Cyclooctatetraene  Jae Sung Park    
    Hückel’s Rule  Citra Rahardjo    
    Annulenes  Tina Lee    
    Aromatic Ions  Julia Yankin    
    Heterocyclic Aromatic Compounds  Amy Tsuchiyama    
    Heterocyclic Aromatic Compounds and Hückel’s Rule  Nico Cadiz    
    The Hammett Equation      
    Representative Electrophilic Aromatic Substitution  Tahmina Yousuf    
    Reactions of Benzene  Tahmina Yousuf    
    Mechanistic Principles of Electrophilic Aromatic Substitution
    Nitration of Benzene  dorota krasecka, Indah Kusumawardhani    
    Sulfonation of Benzene  Alisha Polido    
    Friedel–Crafts Alkylation of Benzene  Monica Pastor    
    Friedel–Crafts Acylation of Benzene  Euna Kim    
    Synthesis of Alkylbenzenes by Acylation–Reduction Amanda Setiawan    
    Rate and Regioselectivity in Electrophilic Aromatic Substitution  Philip Thatcher    
    Rate and Regioselectivity in the Nitration of Toluene      
    Rate and Regioselectivity in the Nitration of (Trifluoromethyl)benzene      
    Substituent Effects in Electrophilic Aromatic Substitution: Activating Substituents  Amy Tsuchiyama    
    Substituent Effects in Electrophilic Aromatic Substitution: Strongly Deactivating Substituents  Nico Cadiz    
    Substituent Effects in Electrophilic Aromatic Substitution: Halogens  Anh Do    
    Multiple Substituent Effects  Anh Do    
    Regioselective Synthesis of Disubstituted Aromatic Compounds  Eriko Iseki    
    Substitution in Naphthalene      
    Substitution in Heterocyclic Aromatic Compounds      
    Principles of Molecular Spectroscopy: Electromagnetic Radiation      
    Principles of Molecular Spectroscopy: Quantized Energy States      
     1H NMR Spectroscopy     
    Nuclear Shielding and 1H Chemical Shifts  Philip Thatcher    
    Effects of Molecular Structure on 1H Chemical Shifts  Citra Rahardjo    
    Ring Currents: Aromatic and Antiaromatic  Junghee Woo    
    Interpreting 1H NMR Spectra  Philip Thatcher    
    Spin–Spin Splitting in 1H NMR Spectroscopy      
    Splitting Patterns: The Ethyl Group      
    Splitting Patterns: The Isopropyl Group      
    Splitting Patterns: Pairs of Doublets      
    Complex Splitting Patterns      
    1H NMR Spectra of Alcohols  Erin Lavin  :)    
    Case Study: Magnetic Resonance Imaging (MRI)      
    NMR and Conformations      
    13C Chemical Shifts  Philip Thatcher    
    13C NMR and Peak Intensities      
    13C 1H Coupling      
    Using DEPT to Count Hydrogens Attached to 13C      
    2D NMR: COSY and HETCOR  Jae Sung Park    
    Introduction to Infrared Spectroscopy  Junghee Woo    
    Case Study: Spectra by the Thousands      
     Infrared Spectra     
    Characteristic Absorption Frequencies  Philip Thatcher    
    Ultraviolet-Visible (UV-VIS) Spectroscopy  Jae Sung Park    
    Mass Spectrometry  Citra Rahardjo    
    Molecular Formula as a Clue to Structure  Philip Thatcher    
    Gas Chromatography, GC/MS, and MS/MS      
    Calculating Aromatic13C Chemical Shifts      
      Ethers, Epoxides, and Sulfides    
    Nomenclature of Ethers, Epoxides, and Sulfides  Tahmina Yousuf    
    Structure and Bonding in Ethers and Epoxides  Sehwan Oh    
    Physical Properties of Ethers  Dorota Krasecka    
    Crown Ethers  Amy Tsuchiyama    
    Preparation of Ethers  Amy Tsuchiyama    
    Case Study: Polyether Antibiotics      
    The Williamson Ether Synthesis  Monica Pastor    
     Reactions of Ethers: A Review and a Preview     
    Acid-Catalyzed Cleavage of Ethers  Andrew Kim, Indah Kusumawardhani    
    Preparation of Epoxides: A Review and a Preview  Tina Lee    
    Conversion of Vicinal Halohydrins to Epoxides  Euna Kim    
    Reactions of Epoxides: A Review and a Preview    
    Nucleophilic Ring Opening of Epoxides  Julia Yankin    
    Acid-Catalyzed Ring Opening of Epoxides  Taehoon Ji, Shierly Mayasari     
    Epoxides in Biological Processes      
    Preparation of Sulfides      
    Oxidation of Sulfides: Sulfoxides and Sulfones      
    Alkylation of Sulfides: Sulfonium Salts      
    Spectroscopic Analysis of Ethers, Epoxides, and Sulfides      
    Case Study: Epoxide Rearrangements and the NIH Shift      
     Aldehydes and Ketones     
    Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group  Nico Cadiz    
    Nomenclature  Amy Tsuchiyama    
    Structure and Bonding: The Carbonyl Group      
    Physical Properties  Monica Pastor    
    Sources of Aldehydes and Ketones      
    Reactions of Aldehydes and Ketones: A Review And a Preview  Anh Do    
    Principles of Nucleophilic Addition: Hydration of Aldehydes and Ketones  Amy Tsuchiyama    
    Cyanohydrin Formation  Monica Pastor    
    Acetal Formation  Jae Sung Park    
    Acetals as Protecting Groups  Tina Lee    
    Reaction with Primary Amines: Imines  Alisha Polido    
    Case Study: Imines in Biological Chemistry      
    Reaction with Secondary Amines: Enamines  Amanda Setiawan    
    The Wittig Reaction  Citra Rahardjo    
    Planning an Alkene Synthesis via the Wittig Reaction  Alisha Polido, Shierly Mayasari     
    Stereoselective Addition to Carbonyl Groups  Amanda Setiawan    
    Oxidation of Aldehydes  Anh Do    
    Baeyer–Villiger Oxidation of Ketones  Tina Lee    
    Spectroscopic Analysis of Aldehydes and Ketones  Sehwan Oh    
    Alcohols, Aldehydes, and Carbohydrates  Eriko Iseki    
     Enols and Enolates    
    The alpha-Hydrogen and Its pKa  Monib Hai    
    The Aldol Condensation  Anh Do    
    Mixed Aldol Condensations  Amanda Setiawan    
    Alkylation of Enolate Ions  Amanda Setiawan    
    Enolization and Enol Content  Junghee Woo    
    Stabilized Enols  Sehwan Oh    
    Halogenation of Aldehydes and Ketones  Jae Sung Park, Shierly Mayasari    
    Mechanism of Halogenation of Aldehydes and Ketones      
    The Haloform Reaction  Amanda Setiawan    
    Some Chemical and Stereochemical Consequences of Enolization      
    The Haloform Reaction and the Biosynthesis of Trihalomethanes      
    Effects of Conjugation in ,-Unsaturated Aldehydes and Ketones      
    Conjugate Addition to ,-Unsaturated Carbonyl Compounds  Eriko Iseki    
    Addition of Carbanions to ,-Unsaturated Ketones: The Michael Reaction  Taehoon Ji    
    Conjugate Addition of Organocopper Reagents o ,-Unsaturated Carbonyl Compounds  Julia Yankin    
    Enolate Regiochemistry and Stereochemistry  Jae Sung Park    
     Carboxylic Acids    
    Carboxylic Acid Nomenclature  Nico Cadiz    
    Structure and Bonding      
    Physical Properties  Nico Cadiz    
    Acidity of Carboxylic Acids  Amy Tsuchiyama    
    Salts of Carboxylic Acids      
    Substituents and Acid Strength  Tahmina Yousuf    
    Ionization of Substituted Benzoic Acids      
    Dicarboxylic Acids      
    Carbonic Acid      
    Sources of Carboxylic Acids      
    Synthesis of Carboxylic Acids by the Carboxylation of Grignard Reagents  Alisha Polido    
    Synthesis of Carboxylic Acids by the Preparation and Hydrolysis of Nitriles Amanda Setiawan     
    Reactions of Carboxylic Acids: A Review and a Preview      
    Mechanism of Acid-Catalyzed Esterification  Eriko Iseki    
    Intramolecular Ester Formation: Lactones      
    Alpha Halogenation of Carboxylic Acids: The Hell–Volhard–Zelinsky Reaction  Andrew Kim    
    Decarboxylation of Malonic Acid and Related Compounds  Andrew Kim    
    Spectroscopic Analysis of Carboxylic Acids  Erin Lavin    
    Lactonization Methods      
    Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution  Tina Lee    
    Nomenclature of Carboxylic Acid Derivatives  Euna Kim    
    Structure and Reactivity of Carboxylic Acid Derivatives      
    General Mechanism for Nucleophilic Acyl Substitution  Sehwan Oh    
    Nucleophilic Acyl Substitution in Acyl Chlorides  Alisha Polido    
    Nucleophilic Acyl Substitution in Carboxylic Acid Anhydrides      
    Physical Properties of Esters      
    Reactions of Esters: A Review and a Preview      
    Acid-Catalyzed Ester Hydrolysis  Andrew Kim    
    Ester Hydrolysis in Base: Saponification  Eriko Iseki    
    Reaction of Esters with Ammonia and Amines      
    Hydrolysis of Amides  Sehwan Oh    
    Lactams  Indah Kusumawardhani             
    Case Study: beta-Lactam Antibiotics      
    Preparation of Nitriles  Taehoon Ji    
    Hydrolysis of Nitriles  Sehwan Oh    
    Addition of Grignard Reagents to Nitriles  Taehoon ji    
    Spectroscopic Analysis of Carboxylic Acid Derivatives  Erin Lavin    
     Ester Enolates    
    Ester Hydrogens and Their pKa’s  Philip Thatcher    
    The Claisen Condensation  Anh Do    
    Intramolecular Claisen Condensation: The Dieckmann Reaction  Philip Thatcher    
    Mixed Claisen Condensations  Jae Sung Park, Shierly Mayasari     
    Acylation of Ketones with Esters  Eriko Iseki    
    Ketone Synthesis via -Keto Esters  Junghee Woo    
    The Acetoacetic Ester Synthesis  Eriko Iseki    
    The Malonic Ester Synthesis  Erin Lavin, Indah Kusumawardhani    
    Michael Additions of Stabilized Anions      
    Reactions of LDA-Generated Ester Enolates      
    The Enolate Chemistry of Dianions      
    Amine Nomenclature      
    Structure and Bonding of Amines      
    Physical Properties of Amines  Monica Pastor    
    Basicity of Amines  Tuba Nemati    
    Amines as Natural Products      
    Tetraalkylammonium Salts as Phase-Transfer Catalysts      
    Reactions That Lead to Amines: A Review and a Preview      
    Preparation of Amines by Alkylation of Ammonia      
    The Gabriel Synthesis of Primary Alkylamines  Citra Rahardjo    
    Preparation of Amines by Reduction Nico Cadiz     
    Reductive Amination  Taehoon Ji    
    Reactions of Amines: A Review and a Preview      
    Reaction of Amines with Alkyl Halides  Amanda Setiawan, Shierly Mayasari    
    The Hofmann Elimination  Tina Lee    
    Electrophilic Aromatic Substitution in Arylamines  Monib Hai    
    Nitrosation of Alkylamines  Taehoon Ji    
    Nitrosation of Arylamines  Andrew Kim    
    Synthetic Transformations of Aryl Diazonium Salts  Euna Kim    
    Azo Coupling      
    Case Study: From Dyes to Sulfa Drugs      
    Spectroscopic Analysis of Amines      
    Synthetic Applications of Enamines  Junghee Woo    
     Aryl Halides    
    Bonding in Aryl Halides      
    Sources of Aryl Halides      
    Physical Properties of Aryl Halides      
    Reactions of Aryl Halides: A Review and a Preview      
    Nucleophilic Substitution in Nitro-Substituted Aryl Halides  Tuba Nemati    
    The Addition–Elimination Mechanism of Nucleophilic Aromatic Substitution  Eriko Iseki    
    Related Nucleophilic Aromatic Substitution Reactions  Euna kim, Shierly Mayasari     
    The Elimination–Addition Mechanism of Nucleophilic Aromatic Substitution: Benzyne  Anh Do    
    Diels–Alder Reactions of Benzyne  Tuba Nemati    
    m-Benzyne and p-Benzyne      
    The Heck Reaction      
    Nomenclature of Phenols  Monica Pastor    
    Structure and Bonding of Phenols      
    Physical Properties of Phenols  Tina Lee    
    Acidity of Phenols  Tuba Nemati    
    Substituent Effects on the Acidity of Phenols  Tuba Nemati    
    Sources of Phenols      
    Naturally Occurring Phenols      
    Reactions of Phenols: Electrophilic Aromatic Substitution  Nico Cadiz    
    Acylation of Phenols  Andrew Kim    
    Carboxylation of Phenols: Aspirin and the Kolbe–Schmitt Reaction  Eriko Iseki    
    Preparation of Aryl Ethers  Andrew Kim    
    Case Study: Agent Orange and Dioxin      
    Cleavage of Aryl Ethers by Hydrogen Halides      
    Claisen Rearrangement of Allyl Aryl Ethers Amanda Setiawan    
    Oxidation of Phenols: Quinones  Citra Rahardjo    
    Spectroscopic Analysis of Phenols  Junghee Woo    
    Directed Metalation of Aryl Ethers      
    Classification of Carbohydrates  dorota krasecka    
    Fischer Projections and D–L Notation  Monica Pastor    
    The Aldotetroses  Nico Cadiz    
    Aldopentoses and Aldohexoses  Amy Tsuchiyama,Tahmina Yousuf    
    A Mnemonic for Carbohydrate Configurations      
    Cyclic Forms of Carbohydrates: Furanose Forms  Anh Do    
    Cyclic forms of Carbohydrates: Pyranose Forms  Tina Lee    
    Mutarotation and the Anomeric Effect  Philip Thatcher    
    Ketoses  Sehwan Oh    
    Deoxy Sugars  Erin Lavin    
    Amino Sugars  Tahmina Yousuf    
    Branched-Chain Carbohydrates      
    Glycosides  Taehoon Ji    
    Disaccharides  Dorota Krasecka    
    Polysaccharides  Junghee Woo    
    Case Study: How Sweet It Is!      
    Reactions of Carbohydrates  Julia Yankin, Shierly Mayasari     
    Reduction of Monosaccharides  Euna Kim    
    Oxidation of Monosaccharides  Junghee Woo    
    Cyanohydrin Formation and Chain Extension      
    Epimerization, Isomerization, and Retro-Aldol cleavage  Tuba Nemati    
    Acylation and Alkylation of Hydroxyl Groups  Jae Sung Park    
    Periodic Acid Oxidation  Amanda Setiawan    
    Emil Fischer and the Structure of (+)-Glucose      
    Acetyl Coenzyme A      
    Fats, Oils, and Fatty Acids  Monica Pastor    
    Fatty Acid Biosynthesis      
    Phospholipids  Monica Pastor    
    Waxes  Junghee Woo    
    Prostaglandins  Tuba Nemati    
    Case Study:  Nonsteroidal Antiinflammatory Drugs (NSAIDS) and COX-2 Inhibitors 1078      
    Terpenes: The Isoprene Rule      
    Isopentenyl Pyrophosphate: The Biological Isoprene Unit      
    Carbon–Carbon Bond Formation in Terpene Biosynthesis      
    The Pathway from Acetate to Isopentenyl Diphosphate      
    Steroids: Cholesterol

     Roland Stern

    Vitamin D  Anh Do    
    Case Study: Good Cholesterol? Bad Cholesterol? What’s the Difference?      
    Bile Acids      
    Corticosteroids  Alisha Polido    
    Sex Hormones  Tuba Nemati    
    Carotenoids  Andrew Kim    
    Anabolic Steroids  Monib Hai    
    Case Study: Crocuses Make Saffron from Carotenes      
     Amino Acids, Peptides, and Proteins    
    Classification of Amino Acids      
    Stereochemistry of Amino Acids  Nico Cadiz    
    Acid–Base Behavior of Amino Acids  Tuba Nemati    
    Synthesis of Amino Acids      
    Reactions of Amino Acids      
    Some Biochemical Reactions of Amino Acids      
    Introduction to Peptide Structure Determination      
    Amino Acid Analysis      
    Partial Hydrolysis of Peptides      
    End Group Analysis      
    Insulin  Monica Pastor    
    The Edman Degradation and Automated Sequencing of Peptides      
    Case Study: Peptide Mapping and MALDI Mass Spectrometry      
    The Strategy of Peptide Synthesis      
    Amino Group Protection  Junghee Woo    
    Carboxyl Group Protection  Tahmina Yousuf    
    Peptide Bond Formation  Jae Sung Park    
    Solid-Phase Peptide Synthesis: The Merrifield Method      
    Secondary Structures of Peptides and Proteins  Dorota krasecka    
    Tertiary Structure of Polypeptides and Proteins  Jae Sung Park    
    Protein Quaternary Structure: Hemoglobin  Julia Yankin    
    Amino Acids in Enantioselective Synthesis      
     Nucleosides, Nucleotides, and Nucleic Acids    
    Pyrimidines and Purines  Nico Cadiz    
    Nucleosides Anh Do    
    Nucleotides  Tuba Nemati    
    ATP and Bioenergetics      
    Phosphodiesters, Oligonucleotides, and Polynucleotides      
    Nucleic Acids  Monib Hai    
    Secondary Structure of DNA: The Double Helix      
    “It Has Not Escaped Our Notice . . .”      
    Tertiary Structure of DNA: Supercoils      
    Replication of DNA      
    Ribonucleic Acids  Philip Thatcher    
    Protein Biosynthesis  Philip Thatcher    
    RNA World      
    DNA Sequencing  Euna kim    
    The Human Genome Project      
    DNA Profiling and the Polymerase Chain Reaction      
    Oligonucleotide Synthesis      
     Synthetic Polymers    
    Some Background      
    Polymer Nomenclature      
    Classification of Polymers: Reaction Type  Euna Kim, Shierly Mayasari     
    Classification of Polymers: Chain-Growth and Step-Growth  Citra Rahardjo    
    Classification of Polymers: Structure  Amy Tsuchiyama    
    Classification of Polymers: Properties  Taehoon Ji    
    Addition Polymers: A Review and a Preview      
    Chain Branching in Free-Radical Polymerization  Taehoon Ji    
    Anionic Polymerization: Living Polymers      
    Cationic Polymerization  Euna kim, Shierly Mayasari     
    Polyamides  Citra Rahardjo    
    Polyesters  Sehwan Oh    
    Polycarbonates  Andrew Kim    
    Polyurethanes  Roland Stern    
    Copolymers  Amy Tsuchiyama    
    Chemical Modification of Polymers