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ChemWiki i-clicker Organic Questions

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.


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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