Chem 227 : Assignments / Activities
Activity 5 (Worksheet)
- Aromaticity |
Activity 6 (Worksheet)
- Electrophilic Aromatic Subs. |
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Activity 7 (Worksheet) - Nucleophilic Aromatic
Subs. |
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Library Research / Calibrated Peer Review (CPR)
LABORATORY
Reading / Homework:
Key Topics are emphasized in Bold Red. Homework problems will serve as examples for some of the types of questions that will be on exams and quizzes. (Most all of the textbook problems are included. There are only a few selected ones that are omitted. If you don't care to rationalize which are which from the lists that follow you can simplify the process by doing them all.)
Chapter:
13. Mass Spectrometry and Infrared Spectroscopy.Mass Spectrometry. The Mass Spectrum. Fragmentation. Isotopes in Mass Spectrometry. Determination of Molecular Formulas: High-Resolution Mass Spectrometry. Fragmentation at Functional Groups. Spectroscopy and the Electromagnetic Spectrum. Infrared Spectroscopy. Infrared Absorption Bands. Intensity of Absorption Bands. Position of Absorption Bands. C-H Absorption Bands. Shape of Absorption Bands. Absence of Absorption Bands. Infrared Inactive Vibrations. Identifying Infrared Spectra. Ultraviolet and Visible Spectroscopy. The Beer-Lambert Law. Effect of Conjugation on <F128>lmax. The Visible Spectrum and Color. Uses of UV/Vis Spectroscopy.
Problems: 1-5,8-20,8-29,32,33a,34,41-47,50,51,54
14. NMR Spectroscopy.Introduction to NMR Spectroscopy. Fourier Transform NMR. Shielding. The Number of Signals in the 1H NMR Spectrum. The Chemical Shift. The Relative Position of 1H NMR Signals. Characteristic Values of Chemical Shifts. Integration of the NMR Signals. Diamagnetic Anisotropy. Splitting of the Signals. More Examples of 1H NMR Spectra. Coupling Constants. Splitting Diagrams. Time Dependence of NMR Spectroscopy. Protons Bonded to Oxygen and Nitrogen. Use of Deuterium in 1H NMR Spectroscopy. Resolution of 1H NMR Spectra. 13C NMR Spectroscopy. DEPT 13C NMR Spectra. Two-Dimensional NMR Spectroscopy. Magnetic Resonance Imaging.
Problems: 3-7,9-32, 34-54,57,58,60-62,64,67,69,-73
V. AROMATIC COMPOUNDS.
15. Aromaticity& Reactions of Benzene.Criteria for Aromaticity. Aromatic Hydrocarbons. Aromatic Heterocyclic Compounds. Some Chemical Consequences of Aromaticity. Antiaromaticity. A Molecular Orbital Description of Aromaticity and Antiaromaticity. Nomenclature of Monosubstituted Benzenes. How Benzene Reacts. General Mechanism for Electrophilic Aromatic Substitution Reactions. Halogenation of Benzene. Nitration of Benzene. Sulfonation of Benzene. Friedel-Crafts Alkylation of Benzene. Friedel-Crafts Alkylations of Benzene. Alkylations of Benzene by Acylation-Reduction.
Problems: 1,2,4-11,15-38
16. Reactions of Substituted Benzenes.Nomenclature of Diubstituted and Polysubstituted Benzenes. Reactions of Substituents on Benzene. The Effect of Substituents on Reactivity. The Effect of Substituents on Orientation. The Effect of Substituents on pK a. The Ortho/Para Ratio. Additional Considerations Regarding Substituent Effects. Designing a Synthesis III: Synthesis of Monosubstituted and Disubstituted Benzenes. Synthesis of Trisubstituted Benzenes. Synthesis of Substituted Benzenes Using Arenediazonium Salts. The Arenediazonium Ion as an Electrophile. Mechanism for the Reaction of Amines with Nitrous Acid. Nucleophilic Aromatic Substitution Reactions. Benzyne. Polycyclic Benzenoid Hydrocarbons. Electrophilic Substitution Reactions of Naphthalene and Substituted Naphthalenes.
Problems: 1-3,5,7,8,10-18,20,22,28-34,38-48,50-58,61-63,67
VI. CARBONYL COMPOUNDS.
17. Carbonyl Compounds I: Nucleophilic Acyl Substitution.Nomenclature. Structures of Carboxylic Acids and Carboxylic Acid Derivatives. Physical Properties of Carbonyl Compounds. Naturally Occurring Carboxylic Acids and Carobxylic Acid Derivatives. How Class I Carbonyl Compounds React. Relative Reactivities of Carboxylic Acids, Acyl Halides, and Carboxylic Acid Derivatives. General Mechanism for Nucleophilic Acyl Substitution Reactions. Reactions of Acyl Halides. Reactions of Acid Anhydrides. Reactions of Esters. Acid-Catalyzed Ester Hydrolysis. Hydroxide-Ion-Promotes Ester Hydrolysis. Soaps, Detergents, and Micelles. Reactions of Carboxylic Acids. Reactions of Amides. Acid-Catalyzed Hydrolysis of Amides. Hydrolysis of an Imide- The Gabriel Synthesis. Hydrolysis of Nitriles. Designing a Synthesis IV: The Synthesis of Cyclic Compounds. Synthesis of Carboxylic Acid Derivatives. Dicarboxylic Acids and Their Derivatives.
Problems: Do all as time allows.
18. Carbonyl Compounds II: Nucleophilic Acyl Addition, Nucleophilic Acyl Substitution, and Nucleophilic Addition-Elimination—Reactions of <F128>a, <F128>b-Unsaturated Carbonyl Compounds.Nomenclature. Relative Reactivities of Carbonyl Compounds. How Aldeyhdes and Ketones React. Reactions of Carbonyl Compounds with Carbon Nucleophiles. Reactions of Carbonyl Compounds with Hydride Ion. Reactions of Aldehydes and Ketones with Nitrogen Nucleophiles. Reactions of Aldehydes and Ketones with Oxygen Nucleophiles. Protecting Groups. Addition of Sulfur Nucleophiles. The Wittig Reaction. Stereochemistry of Nucleophilic Addition Reactions: Re and Si Faces. Designing a Synthesis V: The Synthesis of Cyclic Compounds. Nucleophilic Addition to -Unsaturated Aldehydes and Ketones: Direct Addition Versus Conjugate Addition. Nucleophilic Addition to <F128>a, <F128>b-Unsaturated Carboxylic Acid Derivatives. Enzyme-Catalyzed Additions to <F128>a, <F128>b-Unsaturated Carbonyl Compounds.
Problems: Do all as time allows.
19. Carbonyl Compounds III: Reactions at the <F128>a-Carbon.Acidity of <F128>a-Hydrogens. Keto-Enol Tautomerism. How Enols and Enolate Ions React. Halogenation of the <F128>a-Carbon of Aldehydes and Ketones. Halogenation of the <F128>a-Carbon of Carboxylic Acids: The Hell-Volhard-Zelinski Reaction. <F128>a-Halogenated Carbonyl Compounds in Synthesis. Using LDA to Form an Enolate. Alkylation of the <F128>a-Carbon of Carbonyl Compounds. Alkylation and Acylation of the <F128>a-Carbon via an Enamine Intermediate. Alkylation of the <F128>b-Carbon: The Michael Reaction. The Aldol Addition. Dehydration of Aldol Addition Products: Formation of <F128>a, <F128>b-Unsaturated Aldehydes and Ketones. The Mixed Aldol Addition. The Claisen Condensation. The Mixed Claisen Condensation. Intramolecular Condensation and Addition Reactions. Decarboxylation of 3-Oxocarboxylic Acids. The Malonic Ester Synthesis: Synthesis of Carboxylic Acids. The Acetoacetic Ester Synthesis: Synthesis of Methyl Ketones. Designing a Synthesis VI: Making New Carbon-Carbon Bonds. Reactions at the <F128>a-Carbon in Biological Systems.
Problems: Do all as time allows.
VII. BIOORGANIC COMPOUNDS.
20. More About Oxidation-Reduction Reactions.Reduction Reactions. Oxidation of Alcohols. Oxidation of Aldehydes and Ketones. Oxidation of Alkenes with Peroxyacids. Hydroxylation of Alkenes. Oxidative Cleavage of 1,2-Diols. Oxidative Cleavage of Alkenes: Ozonolysis. Oxidative Cleavage of Alkynes. Designing a Synthesis VII: Functional Group Interconversion. Biological Oxidation-Reduction Reactions. Oxidation of Hydroquinones/Reduction of Quinones.
Problems: Do all as time allows.
21. More about Amines& Heterocyclic Compounds.More About Nomenclature. More About Acid-Base Properties. Amine Inversion. Synthesis of Amines. Reactions of Amines. Reactions of Quaternary Ammonium Compounds. Phase-Transfer Catalysis. Unsaturated Five-Membered-Ring Heterocycles. Unsaturated Six-Membered-Ring Heterocycles. Biologically Important Heterocycles.
Problems: Do all as time allows.
22. Carbohydrates.Classification of Carbohydrates. The D and L Notation. Configurations of the Aldoses. Configurations of the Ketoses. Redox Reactions of Monosaccharides. Osazone Formation. Chain Elongation: The Kiliani-Fischer Synthesis. Chain Shortening: The Ruff Degradation. Stereochemistry of Glucose: The Fischer Proof. Cyclic Structure of Monosaccharides: Hemiacetal Formation. Stability of Glucose. Acylation and Alkylation of Monosaccharides. Formation of Glycosides. The Anomeric Effect. Reducing and Nonreducing Sugars. Determination of Ring Size. Disaccharides. Polysaccharides. Some Naturally Occurring Products Derived from Carbohydrates. Carbohydrates on Cell Surfaces. Synthetic Sweeteners.
Problems: Do all that relate to reading as time allows.
23. Amino Acids, Peptides, and Proteins.Classification and Nomenclature of Amino Acids. Configuration of Amino Acids. Acid-Base Properties of Amino Acids. The Isoelectric Point. Separation of Amino Acids. Resolution of Racemic Mixtures of Amino Acids. Peptide Bonds and Disulfide Bonds. Some Interesting Peptides. Strategy of Peptide Bond Synthesis: N-Protection and C-Activation. Automated Peptide Synthesis. Protein Structure. Determining the Primary Structure of a Protein. Secondary Structure of Proteins. Tertiary Structure of Proteins. Quaternary Structure of Proteins. Protein Denaturation.
Problems: Do all as time allows.
24. Catalysis.Catalysis in Organic Reactions. Nucleophilic Catalysis. Acid Catalysis. Base Catalysis. Metal-Ion Catalysis. Intramolecular Reactions. Intramolecular Catalysis. Catalysis in Biological Reactions. Enzyme-Catalyzed Reactions. Catalytic Antibodies and Artificial Enzymes.
25. The Organic Mechanisms of the Coenzymes—Metabolism.Overall View of Metabolism. Niacin: The Vitamin Needed for Many Redox Reactions. Flavin Adenine Dinucleotide and Flavin Mononucleotide: Vitamin B2. Thiamine Pyrophosphate: Vitamin B1. Biotin: Vitamin H. Pyridoxal Phosphate: Vitamin B6. Coenzyme B12: Vitamin B12. Tetrahydrofolate: Folic Acid. Vitamin KH2: Vitamin K.
VIII: SPECIAL TOPICS IN ORGANIC CHEMISTRY.
26. Lipids.Fatty Acids. Waxes. Fats and Oils. Membranes. Prostaglandins. Terpenes. Vitamin A. Biosynthesis of Terpenes. Steroids. Biosynthesis of Cholesterol. Synthetic Steroids.
Problems: Do all as time allows.
27. Nucleosides, Nucleotides, and Nucleic Acids I.Nucleosides and Nucleotides. ATP: The Carrier of Chemical Energy. Three Mechanisms for Phosphoryl Transfer Reactions. The “High-Energy” Character of Phosphoanhydride Bonds. Kinetic Stability of ATP in the Cell. Other Important Nucleotides. The Nucleic Acids. Helical Forms of DNA. Biosynthesis of DNA: Replication. Biosynthesis of Messenger RNA: Transcription. Ribosomal RNA. Transfer RNA. Biosynthesis of Proteins: Translation. Why DNA Contains Thymine Instead of Uracil. Determining the Base Sequence of DNA. Laboratory Synthesis of DNA Strands. Rational Drug Design.
Problems: Do all as time allows.
28. Synthetic Polymers.General Classes of Synthetic Polymers. Chain-Growth Polymers. Stereochemistry of Polymerization. Ziegler-Natta Catalysts. Polymerization of Dienes. The Manufacture of Rubber. Copolymers. Step-Growth Polymers. Physical Properties of Polymers. Biodegradable Polymers.
Problems: Do all as time allows.
29. Pericyclic Reactions.Three Kinds of Pericyclic Reactions. Molecular Orbitals and Orbital Symmetry. Electrocyclic Reactions. Cycloaddition Reactions. Sigmatropic Rearrangements. Pericyclic Reactions in Biological Systems. Summary of the Selection Rules for Pericyclic Reactions.
30. The Organic Chemistry of Drugs: Discovery and Design.Naming Drugs. Lead Compounds. Molecular Modification. Random Screening. Serendipity in Drug Development. Receptors. Drugs as Enzyme Inhibitors. Designing a Suicide Substrate. Quantitative Structure-Activity Relation-ships (QSAR). Molecular Modeling. Combinatorial Organic Synthesis. Antiviral Drugs. Economics of Drugs. Governmental Regulations.
Activity 1: IR Spectroscopy: Handout [Group] & Exp. 13 Lehman (modified), [Individual]
FORMS: IR (Infrared) Spectrosopy.pdf; MS: Mass Spectrometry.pdf (MS data for the individual unknowns is provided by Dr. R. in response to your e-mail reply to the assignment from first class meeting.)
Infrared Basic Tutorial with six practice problems California State University, Stanislaus
IR Wizard from Steffan (St.) Thomas, University of Potsdam, Germany. A query based tool in English and German. Useful in self-learning-testing applications. Supply a wave number (cm-1) and a table of possibilities is produced with chemical functions that have the value within their range of peak frequencies. Pages are cleanly designed and the built-in search engine works well.
NIST Chemistry Webbook
http://webbook.nist.gov/chemistry
Free government database that includes numerous compounds. Provides
a variety of data: physical, thermodynamic and spectroscopic. IR and
MS spectra available for a portion of the compounds in the data base. An
excellent resource.
Spectral Data Base
System for Organic Compounds
http://www.aist.go.jp/RIODB/SDBS/
SDBS: Integrated Spectral Data Base System for Organic Compounds, a searchable
database that contains: MS (ca 18,000 spectra), 13C NMR (ca 9,700 spectra),
Compound Dictionary, 1H NMR (ca 10,100 spectra, 29,000 compounds) add
IR and Raman.
Interactive
Tutorial: University of Alberta
http://www.chem.ualberta.ca/~orglabs/spectroscopy/specmaster.html
An excellent resource for practice in prediction and interpretation.
Mass Spectrometry:
Mass Spectrometer Animated Tutorial Dr. Thomas Poon, Colby College mass spectrometer Shockwave Interactive Tutorial: Instrument Function, Data Generation, Intrepretation and More. (127 kB)
MS Fragment
Wizard from Steffan (St.) Thomas, University of Potsdam, Germany.
A query based tool in English and German. Useful in self-learning-testing
applications. Supply m/e value and a list of possibilities for the fragment
or mass loss fragment is produced with links to exact mass and isotope
distribution calculators. Pages are cleanly designed and the built-in
search engine works well.
NIST Chemistry Webbook
http://webbook.nist.gov/chemistry
Free government database that includes numerous compounds. Provides a
variety of data: physical, thermodynamic and spectroscopic. IR and MS spectra
available for a portion of the compounds in the data base. An excellent
resource.
MRI Photos
http://www.simplyphysics.com/flying_objects.html
Activity 2: 1H NMR Spectroscopy
FORM: 1H NMR Spectrosopy: Interpretation & Prediction; Reactions.pdf
Interactive Tutorial: University of Alberta
http://www.chem.ualberta.ca/~orglabs/spectroscopy/specmaster.html
An excellent resource for practice in prediction and interpretation.The Basics of NMR: Dr. Joseph Hornak http://www.cis.rit.edu/htbooks/nmr/nmr-main.htm
1 H and 13C NMRs :
Example compound: 1H nmr - example
Prediction & Interpretation: (Could also be Interpretation and Comparison.)
- Identify the protons as equivalent or diastereotopic or enantiotopic.
- Predict the chemical shifts and mutliplicities.
- Draw the spectrum.
- Compare to example.
1H nmr data for your individual unknown is to be generated using the department's 60 MHz FT-NMR spectrometer.
Activity 3: 13C NMR Spectroscopy
FORM: 13C NMR Spectrosopy: Interpretation & Prediction; Reactions.pdf
The Basics of NMR: Dr. Joseph Hornak http://www.cis.rit.edu/htbooks/nmr/nmr-main.htm
1 H and 13C NMRs :
Example compound: 13C nmr - example
Prediction & Interpretation: (Could also be Interpretation and Comparison.)
- Identify the carbons as equivalent or different.
- Predict the chemical shifts and mutliplicities. (Decoupled)
- Draw the spectrum.
- Compare to example.
13C nmr data for your individual unknown is to be generated using the department's 60 MHz FT-NMR spectrometer.
13C nmr: Worksheet spectrum
NMR:
Proton
Chemical Shift Table California State University, Stanislaus
Proton NMR Wizardfrom Steffan (St.) Thomas, University of Potsdam, Germany. A query based nmr tool in English and German. Useful in self-learning/testing applications. Supply a chemical shift value and a table of possibilities is produced with ranges of chemical shifts. Pages are cleanly designed and the built-in search engine works well.
13C Chemical Shift Calculator University of Potsdam, Germany, Produces13C spectra for phenyls, biphenyls, pyridines and pyridazines.
NMR Spectroscopy Problems On-Line:
Prof.
Browne:
University of Alberta
http://www.chem.ualberta.ca/~orglabs/spectroscopy/specmaster.html
Prof. Merlic, UCLA, WebSpectra
http://www.chem.ucla.edu/~webspectra/
Prof. Smith, Notre
Dame
www.nd.edu/~smithgrp/structure/workbook.html
Interpretation:
IR- example, 1H nmr - example,
MS - example, table 13C
nmr - example
Example compound:
Apply IR data , MS data (provided by Dr. R.), and 1H & 13C nmr data to your individual unknown. NMR data generated using the department's 60 MHz FT-NMR spectrometer. Be sure that the structural assignment is complete and accurate.
Spectroscopy for the Organic Chemistry Student from Professor Paul R. Young: University of Illinois, Chicago Organic Chemistry OnLine: Spectroscopy
Integrated Problems (Ten Problems}
Activity 4:
NMR Spectroscopy in Context (handouts)
1) Integrated Spectroscopy and Reaction Chemistry: Analysis of a Draft for Publication - pdf
----- Spectra - pdf
----- Team Form - pdf
"Is Peer Review Broken?", The Scientist, Volume 20 | Issue 2 | Page 26, (February 2006)
http://www.the-scientist.com/article/display/23061/
2) Dehydration of 1-ethyl-2-methylcyclohexanol: NMR application to determine the respective distribution of kinetic and thermodynamic products. See:
NOTE: Check List must be completed as a pre-lab before you may start each lab. You should be able to describe each skill that is to be used in the lab to Dr. R.. Upon lab completion of the lab you should be able to demonstrate and to teach someone the skills that you applied. "Certification" is optional.
Skills & Operations:
Experiments
1. Cleaning and Drying Glassware.2. Using Standard-Taper Glassware.3. Using Glass Rod and Tubing.4. Weighing.5. Measuring Volume.6. Heating.7. Cooling.8. Temperature Monitoring.9. Mixing.10. Addition of Reactants.11. Gravity Filtration.12. Vacuum Filtration.13. Extraction.14. Evaporation.15. Steam Distillation.16. Column Chromatography.17. Thin-Layer Chromatography.18. Paper Chromatography.19. Washing Liquids.20. Drying Liquids.21. Drying Solids.22. Drying and Trapping Gases.23. Recrystallization.24. Sublimation.25. Simple Distillation.26. Vacuum Distillation.27. Fractional Distillation.28. Melting Point.29. Boiling Point.30. Refractive Index.31. Optical Rotation.32. Gas Chromatography.33. High Performance Liquid Chromatography.34. Infrared Spectrometry.35. Nuclear Magnetic Resonance Spectrometry.36. Ultraviolet-Visible Spectrometry.37. Mass Spectrometry.
Electrophilic Aromatic Substitution / Friedel Crafts Acylation (Handouts)Chiral Compounds and Green Chemistry: Reduction of a ketone by sodium borohydride and baker’s yeast (Handouts)
Minilab #37: Hydrolysis Rate of Esters (Handouts)
Insect Repellant: Deet Synthesis- Lehman Exp. 45: Explorations 1, 2, 3Synthesis of a bioregulator: 1-phenyl-3-(4-diethylaminoethoxyphenyl)-2-(E)-propen-1-one (Handouts)
Experiments:
Electrophilic Aromatic Substitution / Friedel Crafts Acylation (Handouts)
a) Nitration Quicktime Movie
b) Bromination Quicktime Movie
c) Acylation Quicktime MovieSummary (Group/Typed) to include: (NOTE: Items #1-4 should follow a common journal format, click here for an example )
1) Reactions and structures (Either drawn with a template [See Dr. R. if you plan this approach] or using ISIS Draw; a free/downloadable drawing program),
2) Concise experimental procedures with % yield of each of the synthesis,
3) IR/NMR spectroscopy data,
4) Physical data: boiling point, index of refraction
5) Answers to the assigned questions; Lehman Questions for final report: #7, pg. 282; #6, pg. 290; #6 & #7 pg. 299
6) Attached copies of each group members raw lab research notebook pages, which should be clearly and legibly written in the format described in the course syllabus to include title, name, date, etc.
7) A typed invoice for NSF that includes the itemized billable man/woman hours for each group member committed to the syntheses, the total hours for the group, the $/hour charge that you think reasonable and the total $ charge. NSFs remittance will be translated into a grade for the group; all members receiving the same grade.
Individual RESULTS & Group Results:
(NOTE: Your individual grade will be subject to adjustment based on the results of a private, confidential survey within the group of each group members performance and contribution.)
Lehman: Minilab 37
Hydrolysis Rate of Esters in strong base: Work in pairs; turn in one completed lab form per group.
Lehman: Experiment 47, Synthesis of Dimedone (modified): Determine the m.p., run the NMR and IR on your product and turn in with:
Questions: Lehman pg. 379, #5 & #9, and:
a) Explain how IR could be used to determine the enol content.
b) Using the nmr spectrum for dimedone that is provided from the link below, calculate the percent of the enol present in the sample.
dimedone NMR
c) Using your value in question b) calculate the equilibrium constant K.
d) Repeat questions b) and c) using your nmr spectrum, calculate the percent difference vs. B) and c), and explain what might cause any differences and how (eg. temperature differences).See similar chemistry that can be used in the preparation of oak moss odorant: http://hjem.get2net.dk/bojensen/Oakmoss/Oakmoss.htm
It illustrates one method of synthesis of 2,4-dihydroxy-3,6-dimethylbenzoic acid methyl ester, the most important odour component in Oakmoss, Evernia prunastri (Usneaceae).
It has a very powerful odour - earthy, woody, phenolic - characteristic of some lichenes, and is much used in perfumery, in low concentration.
References:
1) Sonn A, Berichte 1929;62B:3012
2) Eur.Pat. 133,960 (Chem.Abstr 1986;105:226057x)
3) Bauer K, Garbe D, Surburg H (1990) Common fragrance and flavor materials. Preparation, properties and uses. 2'nd rev. ed. VCH Germany.
Lehman: Minilab 34, Preparation of Aldol Condensation Products(Assignments)
Prepare a "mini"- report following the text's instructions (procedure can be omitted), in addition also include an IR and an NMR with your interpretation of the spectra.
Lehman: Minilab 39, Synthesis of Dimedone DerivativesPrepare a "mini"- report following the text's instructions (procedure can be omitted).
Calibrated Peer Review (CPR)
Design and Development of Drugs
http://cpr.molsci.ucla.edu/1) You are to read an article from the Journal of Chemical Education about organic synthesis and the history of many drugs and medicines,
K.C. Nicolaou, et. al., JChemEd, 75, 1226-1258, (1998); pdf files: Reading-1.pdf; Reading-2.pdf.
2) Learn about the way that one drug (aspirin) was discovered and how chemists contributed to its improvement.
3) Learn to identify new synthetic methods necessary in drug synthesis and future drug development.
4) Learn about a widely used approach to the rapid development of new chemical compounds using Combinatorial Synthesis and how chemical libraries (in a non-traditional sense) are used.
5) Write an essay explaining how aspirin was developed, the methods chemists currently use to develop new and better drugs, which can be applied to any area including nano-materials, and the future of organic synthesis.Library Research
DVC Library
http://www.dvc.edu/library/
DVC On-line Databases
http://www.dvc.edu/library/databases.htmUC Berkeley Chemistry Library & Maps: Campus, Zoom in, Chem Library
Chem Library Homepage: http://www.lib.berkeley.edu/CHEM/
March 2006, UC Berkeley Chem Library Calendar Hours
UCB Pathfinder
http://sunsite2.berkeley.edu:8000/
UC Davis
http://www.lib.ucdavis.edu/
http://www.lib.ucdavis.edu/pse/databases/index.html
University of Texas
http://www.lib.utexas.edu/Libs/Chem/info/
ERIC: Educational Resources Information Center
http://www.eric.ed.gov/
Examples of Some past papers:
Ibogaine
Leinamycin
Ascorbic Acid
Gibberellic Acid
Synthetic Challenges: Earn $$$ for your knowledge and imagination!
For example:
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INNOCENTIVE 861088 Substituted Propionic Acid POSTED: APR 22, 2003 DEADLINE: JUL 30, 2003 $30,000 USD |
Insect Repellant: Deet Synthesis- Lehman Exp. 45:
Refer to: http://ep.llnl.gov/msds/orgchem/Chem227/deet-ex-2005.html(1) Read Lehman pp.353-362 & Chemical Toxicity, Risk & Regulation; (2) Complete Selected/Assigned Exercises from: Malathion: assignments 2005
(2) Complete the synthetic procedure, purify a portion for IR and NMR analysis of your product. Answer questions 5, 6 & 7, pg. 362.
Extra:
See: http://ep.llnl.gov/msds/orgchem/Chem226/ChemComm.htmlRead the linked article "Love Molecules". Identify the structure of the elephant pheromone and outline a synthesis of the compound starting from heptanoic acid lactone, 1-bromopentane, acetic anhydride and any other reagents that you chose.
(3) Enzymes & biological activity
Enzyme Docking (683K QuickTime Movie)
Enzyme catalyzed hydrolysis: Trypsin : p-nitrophenylacetate (498K, QuickTime Movie)
Separation and Identification of Unknown
High Resolution Masses for unknowns
Beynon Table:
http://www.chm.davidson.edu/java/beynon/beynon.html
The Chemistry of Flour:
- http://www.exploratorium.edu/cooking/bread/index.html
http://www.exploratorium.edu/cooking/bread/activity-gluten.html
http://members.lycos.nl/ClassoFoods/ukindex.htmlBread Recipes:
http://www.recipesource.com/baked-goods/breads/
2) List the flours used in increasing order of gluten content and compare them to your ranking of dough elasticity. Explain theoretically what chemical effects lemon juice and salt might have on the elasticity of dough. 3) What pattern in side chain functionality is observed in (a) Highly Hydrophilic amino acids and (b) Hydrophobic amino acids?
4) What two amino acids form the non-nutritive sweetener, Aspartame? Which optical isomers, R- and/or S-, do you think are used in Aspartame? Briefly explain your answer.
Chiral Compounds and Green Chemistry: Reduction of a ketone by sodium borohydride and baker’s yeast
Bio-Recognition: Saccharides, Proteins, Influenza,
SARS, HIV
Click on the above image for the 2003 Performance:
http://chemconnections.llnl.gov/Organic/Chem227/Flu-slides/index.html
Click on the above image for the 2006 Performances:
Influenza
2006 Performances: Movie (17MB)
Synthesis of a bioregulator:
1-phenyl-3-(4-diethylaminoethoxyphenyl)-2-(E)-propen-1-one
Plant Hormones (phytohormones) are divided into five groups:
cytokinins, abscisins, gibberellins, auxins, and ethylene. These groups
interact and control the overall development of plant organs (eg. leaves,
stems, roots, fruit) and effect plant behavior in relation to environmental
conditions. Auxins control cell growth and are involved with plant functions
such as phototropism (growing toward light), suppressing abscission (shedding:
leaves, stalks, fruit, diseased parts), enhancing fruit production, and
inhibiting growth. In this experiment you will prepare a synthetic auxin,
which promotes the production of a carotenoid, lycopene. Carotenoids are
highly conjugated and absorb ultraviolet radiation. They are colored and
provide protection from sunlight and ultraviolet damage.
The synthesis involves two steps. The first is an aldol condensation of
the enolate of acetophenone with p-hydroxybenzaldehyde. The resulting
phenoxide that occurs in the reaction mixture is then directly used as
a nucleophile and reacted with diethyl aminoethyl chloride.
The bioassay of the product measures its effectiveness by determining
the mass percent of lycopene produced by carotogenesis over a period of
several days through the Beer’s Law analysis of the lycopene concentration.
Organize into a group of four. Split the group in half: one half as Team
A and the other Team B. Select which group will do the synthesis: Parts
A & B, and which group will do the bioassay Parts: C & D. One
report will be submitted per group and include the post lab questions.
The entire group is to answer all of the prelab questions before beginning.
The individual Teams are to independently complete the Aldehyde &
Ketone Synthesis Worksheet and Enolate Molecular Modeling exercise.
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Experimental Data / Questions:
Flatulence-II.pdf
Click on each of the birds in the following table one at a time. When opened you will see a page with a colored bird on the left and an empty cage on the right. Focus your eyes on the bird's eye and slowly count to twenty; then quickly shift your view to the center of the empty cage. Record what you observe for each bird and then refer to the color wheel in the Web-link below. Write a brief description relating your results to the color wheel, comparing pairs of colors and their relative locations on the wheel. Also refer to the MC2 emission and absorption spectrum simulation tools to vary colors. These can be linked from the MC2 Java Applets page.
Exercise adapted from the Exploratorium's Snacks: http://www.exploratorium.edu/snacks/bird_in_cage.html
What do you think the color of these cells might be if they were viewable to you?
Based on the experiment done in class,sketch the eye and illustrate where on the retina these cells are located.
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The Human Genome:
1 GCA17 CUC33 GUG | 49 GAU |
2 CCC18 CUA34 AAU | 50 GAC |
3 GUU19 UUU35 AAC | 51 CGU |
4 CUU20 CUG36 CAG | 52 UAG |
5 UUG21 UAU37 UGU | 53 AAG |
6 AUG22 UAC38 CGC | 54 UGG |
7 CCU23 UAA39 GGU | 55 AGG |
8 GCC24 AAA40 GGC | 56 GAG |
9 GCU25 UGA41 GGA | 57 GAA |
10 UCG26 AGA42 GGG | 58 CCG |
11 AUA27 AGC43 CGA | 59 UCC |
12 UUA28 AGU44 CGG | 60 ACC |
13 UUC29 GCG45 UGC | 61 ACU |
14 AUC30 CCA46 CAA | 62 UCU |
15 UCA31 GUC47 CAC | 63 AUU |
16 ACG32 GUA48 CAU | 64 ACA |
(2003)
SARS: Genetic translation
1 HLKNGTCGLVELEKGVLPQLEQPYVFIKRSDALSTNHGHKVVELVAEMDGIQYGRSGI
2 TLGVLVPHVGETPIAYRNVLLRKNGNKGAGGHSYGIDLKSYDLGDELGTDPIEDYEQN
3 WNTKHGSGALRELTRELNGGAVTRYVDNNFCGPDGYPLDCIKDFLARAGKSMCTLSEQ
4 LDYIESKRGVYCCRDHEHEIAWFTERSDKSYEHQTPFEIKSAKKFDTFKGECPKFVFP
5 LNSKVKVIQPRVEKKKTEGFMGRIRSVYPVASPQECNNMHLSTLMKCNHCDEVSWQTC
6 DFLKATCEHCGTENLVIEGPTTCGYLPTNAVVKMPCPACQDPEIGPEHSVADYHNHSN
7 IETRLRKGGRTRCFGGCVFAYVGCYNKRAYWVPRASADIGSGHTGITGDNVETLNEDL
8 LEILSRERVNINIVGDFHLNEEVAIILASFSASTSAFIDTIKSLDYKSFKTIVESCGN
9 YKVTKGKPVKGAWNIGQQRSVLTPLCGFPSQAAGVIRSIFARTLDAANHSIPDLQRAA
10 VTILDGISEQSLRLVDAMVYTSDLLTNSVIIMAYVTGGLVQQTSQWLSNLLGTTVEKL
11 RPIFEWIEAKLSAGVEFLKDAWEILKFLITGVFDIVKGQIQVASDNIKDCVKCFIDVV
12 NKALEMCIDQVTIAGAKLRSLNLGEVFIAQSKGLYRQCIRGKEQLQLLMPLKAPKEVT
13 FLEGDSHDTVLTSEEVVLKNGELEALETPVDSFTNGAIVGTPVCVNGLMLLEIKDKEQ
14 YCALSPGLLATNNVFRLKGGAPIKGVTFGEDTVWEVQGYKNVRITFELDERVDKVLNE
15 KCSVYTVESGTEVTEFACVVAEAVVKTLQPVSDLLTNMGIDLDEWSVATFYLFDDAGE
16 ENFSSRMYCSFYPPDEEEEDDAECEEEEIDETCEHEYGTEDDYQGLPLEFGASAETVR
17 VEEEEEEDWLDDTTEQSEIEPEPEPTPEEPVNQFTGYLKLTDNVAIKCVDIVKEAQSA
18 NPMVIVNAANIHLKHGGGVAGALNKATNGAMQKESDDYIKLNGPLTVGGSCLLSGHNL
19 AKKCLHVVGPNLNAGEDIQLLKAAYENFNSQDILLAPLLSAGIFGAKPLQSLQVCVQT
20 VRTQVYIAVNDKALYEQVVMDYLDNLKPRVEAPKQEEPPNTEDSKTEEKSVVQKPVDV
21 KPKIKACIDEVTTTLEETKFLTNKLLLFADINGKLYHDSQNMLRGEDMSFLEKDAPYM
22 VGDVITSGDITCVVIPSKKAGGTTEMLSRALKKVPVDEYITTYPGQGCAGYTLEEAKT
(2005-2006)
Will Bird Flu mutate and transfer from human to human? Where
did SARS go?
Qual Organic Analyses:
End
of Course Survey: (Anonymous survey)
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