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ChemWiki i-clicker Organic Questions

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

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

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.
Register for an account online via the upper right hand corner of the ChemWiki's front page.
Sign up for the ChemWiki Topics at the bottom of this page. (Enter your name in the table and refer to.)
Pages will not need be constructed.
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.
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.)
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.
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
S_n1 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 pK_a	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 pK_a’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

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ChemWiki i-clicker Organic Questions

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