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ChemWiki i-clicker Organic Questions

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    2058
  • 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 (rrusay@chemconnections.org) 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
    Benzene
    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
    Spectroscopy
    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
    Esters
    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
    Amides
    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
    Thioesters
    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
    Amines
    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
    Phenols
    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
    Carbohydrates
    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
    Lipids
    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
    Polyketides
    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
    Electrophoresis
    Reactions of Amino Acids
    Some Biochemical Reactions of Amino Acids
    Peptides
    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
    Coenzymes
    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
    Bioenergetics
    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
    AIDS
    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