Chem 226: Assignments / Activities
Reading/Homework * Worksheets * Lab Schedule * Experiments * Lab Techniques & Videos

Reading / Homework:

Course topics are listed below. I-clicker questions, Worksheets, Textbook problems, and ACS test questions will serve as examples for many of the types of questions and problems that will be on exams and quizzes.

(Attempting all of the textbook's end of chapter problems is encouraged as your time allows, and refering to the text's solution manual for validation after doing the problems. Clicking on the Chapter heading will link you to solutions for that chapter.)



ORGANIC CHEMISTRY (Klein, 1st ed)

Electronic Structure, Bonding and Shape:VSEPR (Chem 120/121 Review); Acids and Bases (Chem 120/121 Review).

CHAPTER 1
1.1: Introduction to Organic Chemistry
1.2: The Structural Theory of Matter
1.3: Electrons, Bonds, and Lewis Structures
1.4: Identifying Formal Charges
1.5: Induction and Polar Covalent Bonds
1.6: Atomic Orbitals
1.7: Valence Bond Theory
1.8: Molecular Orbital Theory
1.9: Hybridized Atomic Orbitals
1.10: VSEPR Theory: Predicting Geometry
1.11: Dipole Moments and Molecular Polarity
1.12: Intermolecular Forces and Physical Properties
1.13: Solubility

CHAPTER 2
2.1: Molecular Representations
2.2: Bond-Line Structures
2.3: Identifying Functional Groups
2.4: Carbon Atoms with Formal Charges
2.5: Identifying Lone Pairs
2.6: Three-Dimensional Bond-Line Structures
2.7: Introduction to Resonance
2.8: Curved Arrows
2.9: Formal Charges in Resonance Structures
2.10: Drawing Resonance Structures via Pattern Recognition
2.11: Assessing Relative Importance of Resonance Structures
2.12: Delocalized and Localized Lone Pairs

CHAPTER 3
3.1: An Introduction to BrØnsted-Lowry Acids and Bases
3.2: Flow of Electron Density: Curved Arrow Notation
3.3: BrØnsted-Lowry Acidity: A Quantitative Perspective
3.4: BrØnsted-Lowry Acidity: Qualitative Perspective
3.5: Position of Equilibrium and Choice of Reagents
3.6: Choice of Solvent
3.7: Solvating Effects
3.8: Counterions
3.9: Lewis Acids and Bases

CHAPTER 4
4.1: Introduction to Alkanes
4.2: Nomenclature of Alkanes
4.3: Constitutional Isomers of Alkanes
4.4: Relative Stability of Isomeric Alkanes
4.5: Sources and Uses of Alkanes
4.6: Drawing Newman Projections
4.7: Conformational Analysis of Ethane and Propane
4.8: Conformational Analysis of Butane
4.9: Cycloalkanes
4.10: Conformations of Cyclohexane
4.11: Drawing Chair Conformations
4.12: Monosbstituted Cyclohexane
4.13: Disubstituted Cyclohexane
4.14: cis-trans Stereoisomerism
4.15: Polycyclic Systems

CHAPTER 5
5.1: Overview of Isomerism
5.2: Introduction to Stereoisomerism
5.3: Designating Configuration Using the Cahn-Ingold-Prelog System
5.4: Optical Activity
5.5: Stereoisomeric Relationships: Enantiomers and Diastereomers
5.6: Symmetry and Chirality
5.7: Fischer Projections
5.8: Conformationally Mobile Systems
5.9: Resolution of Enantiomers

CHAPTER 6
6.1: Enthalpy
6.2: Entropy
6.3: Gibbs Free Energy
6.4: Equilibria
6.5: Kinetics
6.6: Reading Energy Diagrams
6.7: Nucleophiles and Electrophiles
6.8: Mechanisms and Arrow Pushing
6.9: Combining the Patterns of Arrow Pushing
6.10: Drawing Curved Arrows
6.11: Carbocation Rearrangements

CHAPTER 7
7.1: Introduction to Substitution Reactions
7.2: Alkyl Halides
7.3: Possible Mechanisms for Substitution Reactions
7.4: The SN2 Mechanism
7.5: The SN1 Mechanism
7.6: Drawing the Complete Mechanism of an SN1 Reaction
7.7: Drawing the Complete Mechanism of an SN2 Reaction
7.8: Determining Which Mechanism Predominates
7.9: Selecting Reagents to Accomplish Functional Group Transformation

CHAPTER 8
8.1: Introduction to Elimination Reactions
8.2: Alkenes in Nature and in Industry
8.3: Nomenclature of Alkenes
8.4: Stereoisomerism in Alkenes
8.5: Alkene Stability
8.6: Possible Mechanisms for Elimination
8.7: The E2 Mechanism
8.8: Drawing the Products of an E2 Reaction
8.9: The E1 Mechanism
8.10: Drawing the Complete Mechanism of an E1 Process
8.11: Drawing the Complete Mechanism of an E2 Process 372
8.12: Substitution vs. Elimination: Identifying the Reagent
8.13: Substitution vs. Elimination: Identifying the Mechanism(s)
8.14: Substitution vs. Elimination: Predicting the Products

CHAPTER 9
9.1: Introduction to Addition Reactions
9.2: Addition vs. Elimination: A Thermodynamic Perspective
9.3: Hydrohalogenation
9.4: Acid-Catalyzed Hydration
9.5: Oxymercuration-Demercuration
9.6: Hydroboration-Oxidation
9.7: Catalytic Hydrogenation
9.8: Halogenation and Halohydrin Formation
9.9: Anti Dihydroxylation
9.10: Syn Dihydroxylation
9.11: Oxidative Cleavage
9.12: Predicting Products of an Addition Reaction
9.13: Synthesis Strategies

CHAPTER 10
10.1: Introduction to Alkynes
10.2: Nomenclature of Alkynes
10.3: Acidity of Acetylene and Terminal Alkynes
10.4: Preparing Alkynes
10.5: Reduction of Alkynes
10.6: Hydrohalogenation of Alkynes
10.7: Hydration of Alkynes
10.8: Halogenation of Alkynes
10.9: Ozonolysis of Alkynes
10.10: Alkylation of Terminal Alkynes
10.11: Synthesis Strategies

CHAPTER 11
11.1: Radicals
11.2: Common Patterns in Radical Mechanisms
11.3: Chlorination of Methane
11.4: Thermodynamic Considerations for Halogenation Reactions
11.5: Regioselectivity of Halogenation
11.6: Stereochemistry of Halogenation
11.7: Allylic Bromination
11.8: Atmospheric Chemistry and the Ozone Layer
11.9: Autooxidation and Antioxidants
11.10: Addition of HBr: Anti-Markovnikov Addition
11.11: Radical Polymerization
11.12: Radical Processes in the Petrochemical Industry
11.13: Halogenation as a Synthetic Technique

CHAPTER 12
12.1: One-Step Syntheses
12.2: Functional Group Transformations
12.3: Reactions that Change the Carbon Skeleton
12.4: How to Approach a Synthesis Problem
12.5: Retrosynthetic Analysis
12.6: Practical Tips for Increasing Proficiency
12.5: Retrosynthetic Analysis
12.6: Practical Tips for Increasing Proficiency

CHAPTER 13
13.1: Structure and Properties of Alcohols
13.2: Acidity of Alcohols and Phenols
13.3: Preparation of Alcohols via Substitution or Addition
13.4: Preparation of Alcohols via Reduction
13.5: Preparation of Diols
13.6: Preparation of Alcohols via Grignard Reagents
13.7: Protection of Alcohols
13.8: Preparation of Phenols
13.9: Reactions of Alcohols: Substitution and Elimination
13.10: Reactions of Alcohols: Oxidation
13.11: Biological Redox Reactions
13.12: Oxidation of Phenol
13.13: Synthesis Strategies

CHAPTER 14
14.1: Introduction to Ethers
14.2: Nomenclature of Ethers
14.3: Structure and Properties of Ethers
14.4: Crown Ethers
14.5: Preparation of Ethers
14.6: Reactions of Ethers
14.7: Nomenclature of Epoxides
14.8: Preparation of Epoxides
14.9: Enantioselective Epoxidation
14.10: Ring-Opening Reactions of Epoxides
14.11: Thiols and Sulfides
14.12: Synthesis Strategies Involving Epoxides

 

 


 

(QuizSolutions)

(QuizSolutions)



Worksheets: (Collaborative/Group)

NOTE: Worksheets are in pdf format. You will need Adobe Acrobat Reader to view and print them which can be downloaded for free at: http://www.adobe.com/products/acrobat/readstep2.html

Chemical Bonding Concept Map .pdf

Organic Molecules (1) .pdf (Bonds, Stuctures, Formulas & Shapes)
Related Web-page: http://chemconnections.org/organic/chem226/Labs/VSEPR/

Organic Molecules (2) .pdf (Stuctures, Formulas & Orbitals)

Organic Molecules (3) .pdf (Organic Functional Groups)

Organic Molecules (4) .pdf (Functions, Polarity, Formal Charge)

Organic Molecules (5) .pdf (Acids & Bases) Charge Table .pdf; Charge Table .html

Alkane/Alkene Worksheet (6) .pdf
Refer to:
Hydrocarbon Stabilities / Isomerism: Value for your gasoline dollar.

Conformational Analysis Worksheet (7) Part I .pdf; Part II .pdf
Conformational & Structural Exercises based on Computational Chemistry

Reactions of Alkenes Worksheet (8) .pdf

Stereochemistry I (9).pdf

Stereochemistry II (10) .pdf

Free Radical Reactions/ Stereochemistry .pdf
Product 1 - Product 2

Alkynes: reactions, reagents, synthesis (11) .pdf

Diels Alder .pdf

Molecular Modeling: Diels Alder Reactions (I) .pdf

Molecular Modeling: Diels Alder Reactions (II) .pdf

Halides-Tosylates I .pdf
Halides-Tosylates II .pdf
Halides-Tosylates Synthesis .pdf

Molecular Modeling / Resonance .pdf
Class Assignments

Review .pdf


Laboratory

  1. ORGANIC COMPOUNDS: Preparation / Isolation / Purification / Identification;
  2. SAFETY: General Regulations & Lab Guidelines
    Safety Quiz Sheet & Acknowledgment
  3. LABORATORY EQUIPMENT: Aldrich-Kit with Ground Glass Joints
  4. LABORATORY SKILLS: Organic Lab Skills & Operations Check List
  5. RECORD KEEPING: Research Notebooks & Reports

NOTE: Check List must be completed as part of the pre-lab before you may start any lab experiment. You should be able to describe each skill that is to be used in the lab to Dr. R.. Upon completion of the lab experiment you should be able to demonstrate and to teach someone the skills that you acquired. Before beginning the first lab experiment, you are to review the Lab Text/Guide's Table of Contents relative to the check list and provide the appropriate page numbers for the respective Skill/Operation from the text and your comments on how understandable and complete the text's information is to you. Complete the form and turn-in to Dr. R.

Tentative Lab Schedule: (Refer to the course calendar for more exact details and for Due dates.)
WEEK
DATES
Activity
Experiments
1
Aug 20-24

Lab Check in
Memory / Learning
Chemical Bonding Concept Map

Organic Molecules (1) .pdf (Bonds, Stuctures, Formulas & Shapes)
Related Web-page: http://chemconnections.org/organic/chem226/Labs/VSEPR/


Organic Molecules
(2) .pdf (Stuctures, Formulas & Orbitals)

Smell / Olfaction: (pdf files)
Part I: Odor and  Molecules/ Distinguishing Organic Molecules Based on Odor
Part II: Odor and  Molecular Formulas
2
Aug 27-31

Organic Molecules (3) .pdf (Organic Functional Groups)
Sudoku (3A): Instuctions .pdf, Sudoku #1 .pdf, Sudoku #2 .pdf

Organic Molecules (4) .pdf (Functions, Polarity, Formal Charge)


Smell / Olfaction: (pdf files)
Part III: Odor and  Functionality
Part IV: Chemical Communication

Molecular Modeling I / WebMO / Dipole Moment
Part 1; Part 2

3
Sept 3-7

Lab Drawer / Equipment Check Out
Aldrich-Kit with Ground Glass Joints

MSDS/ Organic Chemistry:Toxicity, Health & Safety (pdf files)

SAFETY: General Regulations & Lab Guidelines
Safety Quiz Sheet & Acknowledgment
Lab Skills & Operations Survey: form

Lab Skills & Operations Check List & prelab

Separation (Isolation):
Solubility / Extraction Demo

 

4
Sept 10-14
Lab Skills & Operations Check List & prelab

Separation (Isolation):
Solubility / Extraction

(Purification)
Recrystallization

Identification:
m.p.

 

5
Sept 17-21
Lab Skills & Operations Check List & prelab

(Purification)
Recrystallization
Identification:
m.p.

 

 

6
Sept 24-28
Lab Skills & Operations Check List & prelab

(Identification)
Analgesics:
TLC

(Preparation)
Synthesis:Salicylic Acid

 

7
Oct 1-5
Lab Skills & Operations Check List & prelab

(Identification)
Analgesics:
TLC

(Preparation)
Synthesis:Salicylic Acid

Enantiomeric Separation/ Polarimetry

8
Oct 8-12
Lab Skills & Operations Check List & prelab
9

Oct 15-19

Lab Skills & Operations Check List & prelab
10
Oct 22-26
Lab Skills & Operations Check List & prelab
11
Oct 29-Nov 1
Lab Skills & Operations Check List & prelab Acetate Synthesis / IR
12
Nov 5-9
Lab Skills & Operations Check List & prelab CPR / Sn1 & Sn2 Reactions
13
Nov 12-16
Lab Skills & Operations Check List & prelab Steam Distillation / Natural Products
14
Nov 19-23
Lab Skills & Operations Check List & prelab

Steam Distillation / Natural Products

Diels Alder / Molecular Modeling

15
Nov 26-30
Lab Skills & Operations Check List & prelab
16
Dec 3-Dec 7
Lab Skills & Operations Check List & prelab
Colorful Grignard
17
Dec 10
Lab Drawer / Equipment Check In
 


Skills & Operations:
Exercises / Activities / Experiments

1. Use & Care of Tapered Glassware.
2. Weighing Techniques: Tare & Care
3. Transferring Liquids.
4. Care, Handling & Storage of Chemicals.
5. Chemical Hygiene & Waste Disposal
6. Temperature: Measurement & Control.
7. Heating Methods.
8. Reflux.
9. Cooling Methods.
10. Methods of Addition (s, l, & g).
11. Filtration (Gravity).
12. Filtration (Vacuum/Aspirator).
13. Extraction.
14. Evaporation.
15. Rotevap: Recovery of Solvents.
16. Column Chromatography.
17. Thin-Layer Chromatography.
18. Gas Chromatography.
19. Washing Liquids.
20. Drying Liquids.
21. Drying Solids.
22. Drying and Trapping Gases.
23. Recrystallization.
24. Sublimation.
25. Steam Distillation.
26. Simple Distillation.
27. Vacuum Distillation.
28. Fractional Distillation.
29. Melting Point Determination.
30. Boiling Point Determination.
31. Refractive Index Determination.
32. Polarimetry: Optical Rotation.
33. IR: Infrared Spectrometry.
34. NMR: Nuclear Magnetic Resonance.
35. Ultraviolet-Visible Spectrometry.
36. Mass Spectrometry.

Learning Styles Survey:
Organic Chemistry / Memory / Learning


Safety:
SAFETY: General Regulations & Lab Guidelines

Safety Quiz Sheet & Acknowledgment

MSDS/ Organic Chemistry:Toxicity, Health & Safety (pdf files)

Part I: Definitions (Individual)
Part II:: MSDS Data acquisition, interpretation, application & communication (Group)
NFPA Hazard Classifications & Placard

Molecular Modeling I / WebMO / Dipole Moment
Part 1; Part 2

Smell / Olfaction: (pdf files)
Part I: Odor and  Molecules/ Distinguishing Organic Molecules Based on Odor
Michael Rossman: A case of anosmia easing incarceration
Part II: Odor and  Molecular Formulas
Part III: Odor and  Functionality
Part IV: Chemical Communication

Chemical Communication html : http://chemconnections.org/organic/chem226/Labs/Smell/ChemComm.html

Smell & Stereochemistry html:
http://chemconnections.org/organic/chem226/Labs/Smell/Smell-Stereochem.html

Molecular Modeling IIConformations

 Molecular Modeling IIa:  Cyclic / Acyclic Hydrocarbons:Material Properties



Experiment #1 (demo):  Extraction (Observed)

Experiment #1:  Extraction

Experiment #2: Recrystallization & Melting Point

Experiment #3:  Thin Layer Chromatography (TLC)
TLC of Analgesic Drug Components


Experiment #4: Synthesis of Salicylic Acid from Wintergreen


Experiment #5: Enantiomeric Separation/ Resolution (Ibuprofen)
Optical Activity /Polarimetry: Part I & Part II
Optical Rotation I .pdf; Optical Rotation II .pdf
; Optical Rotation III .pdf

Experiment #6: Gas Chromatography & Fractional Distillation

Experiment #7: Bromination of Cinnamic Acid

Experiment #8: Acetate Synthesis, Simple Distillation, Infrared Spectroscopy, GC

Experiment #9: Sn1 , Sn2 Reactions and Solvent Effects

Experiment #10: Essential Oils / Steam Distillation / Extraction

Experiment #11: Diels Alder reaction of maleic anhydride and furan

Experiment #12: Identification of Terpenoids

Experiment #13 : Colorful Grignard Reaction

 
   

Laboratory Techniques & Videos:

Techniques:
Extraction:

Thin Layer Chromatography (TLC):

Gas Cromatography:


Column Chromatography:

Simple & Fractional Distillation:

Vacuum Distillation:

Filtration:

Reflux:

Recrystallization:

Melting Point:

Infrared Spectroscopy:

Rotary Evaporation:

Videos:
http://www.chem.ualberta.ca/%7Eorglabs/Techniques.html
http://www.oid.ucla.edu/Webcast/chemistry/index.html
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm

Extraction:
http://www.chem.ualberta.ca/%7Eorglabs/Techniques.html

http://www.oid.ucla.edu/Webcast/chemistry/index.html
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm (Reaction Work-Up I)

Thin Layer Chromatography (TLC):
http://www.oid.ucla.edu/Webcast/chemistry/index.html
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
Gas Cromatography:
http://www.oid.ucla.edu/Webcast/chemistry/index.html
Column Chromatography:
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
Simple & Fractional Distillation:
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
http://www.oid.ucla.edu/Webcast/chemistry/index.html
Vacuum Distillation:
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
Filtration:
http://www.chem.ualberta.ca/%7Eorglabs/Procedures/Filtration/Videos.html
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
Reflux:
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
Recrystallization:
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
http://www.oid.ucla.edu/Webcast/chemistry/index.html
Melting Point:
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
http://www.oid.ucla.edu/Webcast/chemistry/index.html
Infrared Spectroscopy:
http://www.oid.ucla.edu/Webcast/chemistry/index.html
Rotary Evaporation:

http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm (Reaction Work-Up II)

 

 


Laboratory Experiments
These experiments have been adapted from standard types of experiments commonly performed in organic chemistry courses throughout North America. They are derived from the non-copyrighted, open Web source materials kindly made available by a large number of notable educators/professors who generously share their creativity, time, efforts, and excellent materials. Their institutions include: University of Colorado, Boulder; McMaster University; University of Alberta; University of Calgary; Reed College, Barnard University; Massachusettes Institute of Technology; University of California, Los Angeles; Dakota State University; Wellesley University; University of California, Berkeley; Mount Holyoke College, Manhattan College.

Solubility / Extraction / Separation (Observed)

Applying solubility differences in immiscible solvents:
(DEMO) The relative distribution of I2 in a water layer versus an organic solvent layer (Methylene chloride: CH2Cl2) is examined.
This type of solubility difference is the basis for the fundamental way organic chemicals are separated.
 

Extraction: Isolation / Separation of 4-Chloroaniline (p-chloroaniline), Benzoic acid, and 4-Dibromobenzene (p-dibromobenzene)
Prelab questions
See:
Introduction
Procedure / Instructions
Background & Tutorial:
http://www.chem.ualberta.ca/%7Eorglabs/Interactive%20Tutorials/separation/mastercopy/Extraction.htm
Filtration & Liquid/Liquid Extraction:(Videos)
http://www.oid.ucla.edu/Webcast/chemistry/index.html
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm (Reaction Work-Up I)
http://www.chem.ualberta.ca/%7Eorglabs/Techniques.html

 
Post Lab Questions:
  1. Briefly explain why sodium benzoate is more soluble in H2O rather than in ether, but its conjugate acid is more soluble in ether rather than H2O.
  2. The solubility of p-cresol in water at 25 oC is 56.0 g/L and in ether at the same temperature 310.0 g/L. (a) Calculate the value of Kp. (b) For a solution of 2.5 g of p-cresol in 50 mL of water, calculate the weight of p-cresol that would be extracted into 150 mL of ether by (1) a single extraction, and (2) the total weight extracted by three sequential extractions with 50 mL of ether each.
  3. Using extraction and the reagents and solvents from question #3 of the prelab, show a separation scheme with line drawings for the compounds, the appropriate reagents for each step and the solvent used to separate a four component mixture of phenylacetic acid (pKa = 4.28), o-cresol ( pKa = 10.2), o-xylene (a neutral compound,) and quinoline, a base (pKa of quinoline's conjugate acid = 4.90)?

Grading Rubrik
Results 2009


Recrystallization: Purification of an Unknown Solid
See:
Introduction
Procedure / Instructions
Background:
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
http://www.oid.ucla.edu/Webcast/chemistry/index.html

http://www.chem.ualberta.ca/%7Eorglabs/Techniques.html

Melting Point: Identification of an Unknown Solid


See:
Introduction
Procedure / Instructions
Background:
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
http://www.oid.ucla.edu/Webcast/chemistry/index.html

Post Lab Questions:

  1. Turn-in your sample clearly labeled with your name and pertinent information as per the Lab instructions.
  2. Benzoic acid is one component in a two component mixture. The other component is either ortho toluic acid, phenyl succinate or meta aminophenol. Mixed melting points were done with benzoic acid plus each of the three possibilities. The mixture with ortho toluic acid began to melt at 89oC. The mixture with phenyl succinate began to melt at 120oC. The mixture with meta aminophenol began to melt at 102oC. The melting points of the pure compounds are: benzoic acid =121oC, ortho toluic acid = 102 oC, phenyl succinate = 121 oC, and meta aminophenol = 122oC. What is the second compound in the mixture? Explain how you decided.
  3. What properties are necessary and desirable for a single solvent in order that it be well suited for recrystallizing a particular organic compound?
  4. Which of the following mixtures could not be used for two-solvent systems and why?
    (a) acetone-water (b) dichloromethane-water (c) ethanol-water
    (d) ether-water (e) hexane-water (f) toluene-water
  5. Suppose that your sample had contained black colored impurities. How would you modify the recrystallization procedure to provide easy and efficient decolorizing of the sample?
  6. Why is suction filtration preferable to ordinary gravity filtration for separating punfied crystals from the mother liquor? Why should the vacuum be released at the apparatus before turning off the aspirator?
 
Grading Rubrik


Synthesis of Salicylic Acid from Wintergreen Oil

Experimental
Introduction
Procedure / Instructions

Complete Post lab questions:

1. What happened to the methanol produced in the reaction?
2. If you calculated that you needed 10 mL of 3M sulfuric acid but you discover that the only acid available is 6M hydrochloric acid, how many mL would you use?
3.. If the entire salicylic acid sample that you obtained were reacted to produce a 100% yield of aspirin, how much aspirin (mg) would be produced?


(Read the following and answer the related questions):
http://chemconnections.llnl.gov/Organic/Chem226/Announcements-info/aspirin-CEN-8-18-1997.html
http://chemconnections.llnl.gov/Organic/Chem226/Announcements-info/aspirin-econ-8-9-1997.html

a) Who discovered the structure and first synthesized salicylic acid? In what year?

b) Who was awarded a Nobel prize for determining how aspirin works? In what year were the first clinical trials done?

c) If there were 250 mg of aspirin in every tablet sold, how many metric tons of aspirin would be produced each year? Show your calculation.


d)
Provide a generic name for the local hormones which are affected by aspirin; draw a structure for one of them and name it.

e) Explain the relationship of cyclooxygenase (cox) enzymes to analgesic acitivty. What are the diferences between the enzymes cox-1 and cox-2? What may cox-3 be involved with? What is different about "new" improved Tylenol Extra. Why do you think that Johnson & Johnson developed it?


Acetate Synthesis, Simple Distillation, Infrared Spectroscopy, Index of refraction, [GC]

A) Complete the prelab form using the links below to find which ester that you are to synthesize.

Pre-lab: Click on the images or letters below to see which acetate ester.corresponds to each smell. The letters A and B are two different possiblities..
Pre lab questions & form

To discover the ester that you are to synthesize click here to find the randomly assigned fruity smell that it relates to; then complete the pre-lab questions. For questions #2 and #3 choose either A or B for banana and pear respectively, but, if an A or B follows your assigned smell be sure to use that corresponding ester for the pre-lab questions #2 and #3. Refer to: Acetate Boiling Point Table

     
A or B
 
A or B

Experimental
Introduction
Procedure / Instructions

Prepare your lab notebook using the correct alcohol for the assigned smell, include its physical and chemical properties in the data report table for your prelab. Calculate the appropriate amounts of alcohol and glacial acetic acid. Neatly sketch the apparatus (assembly) that you plan to use for the reaction in your notebook.Complete the lab skills check list and then have Dr. R. initial your notebook.

Begin and complete the synthesis after pre lab approval. Record the mass of crude product and calculate the % yield. Run an IR on the crude product.

B) Distill crude product. (Simple distillation.)
Simple Distillation:
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm

C) Identify functions from infrared spectra

1) Refer to IR-Tutor & tutorial: http://wwwchem.csustan.edu/Tutorials/INFRARED.HTM

2) Begin the worksheet, Infrared Analysis (IR) / Synthesis of Acetates .pdf : Unknown spectra (Identify the chemical function present in each Web unknown assigned to you. If your DVC ID ends in an odd number, do the odd Unknowns; if it ends in an even number or zero, do the even. Then, find a partner who has done the other set and explain your assignments of functions and peaks in the spectra that support your choices. Complete the entire form of 10 unknowns. The selection is limited to alcohols, carboxylic acids, esters, ethers, ketones and aldehydes. Be sure to provide the key peak(s) in the spectrum that support your assignment of the function. [NOTE: The molecules contain only C,H,O; there are no nitrogen atoms in the molecules.]

3) Run  FT-IR spectra on 1) your individual unknown liquid and 2) the ester that you synthesized and distilled.


4) Analyze the spectra.
1. What function is present in the liquid unknown? 2. Consider the starting alcohol and glacial acetic acid: are either or both of them present as impurities in your product? What peaks indicate the presence of product (ester)? Are the peaks in either of the reactants? Complete the form: Infrared Analysis (IR) / Synthesis of Acetates .pdf

IR Analysis:
(Works only with Windows PCs and Chime: PS 110 Computers are OK.) http://www.umass.edu/microbio/chime/ir-spect/

D) Determine the product's index of refraction. (Include in lab report with the boiling point of your product.)

Click on the image above for instrument instructions.

E) Analyze Product by GC. (Optional as time and GC availability allows. If completed, include in lab report with calculation of the % purity of your product.)

Post lab questions:
a) Major League Baseball & Chewing Gum (Post lab) Form .pdf

b) Complete Odor, Functions & Structures .pdf (Post lab)
Views of rose oxide isomers: rose oxide #1 and rose oxide #2. Rose oxide #1 is ~100x more powerful in its scent than #2.]

Grading Rubrik


Gas Chromatography & Fractional Distillation

Experimental
Introduction
Procedure / Instructions


VIDEOS:
Gas Cromatography:

http://www.oid.ucla.edu/Webcast/chemistry/index.html
Simple & Fractional Distillation:
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
http://www.oid.ucla.edu/Webcast/chemistry/index.html
General instructions .pdf
Prelab Form .pdf
Pre lab questions .html
CPR Idealized data .pdf

Separations Class
Separations ppt
Separations pdf

Unkown Retention Times

Logger Pro Example

GC Liquid-Stationary Phases

Fractional Distillation /GC Class Data

The fractionating columns below are a packed column on the left and a Vigreaux column on the right.


Post lab QUESTIONS:

1) Recommend a stationary phase, column temperature and helium flow rate to analyze an ester like banana oil, isoamyl acetate.

Read the following and answer the related questions #s 2-4.
NYT-auto-smell.html
NYT-Sniffing-Cars.html
VOCs-C&EN.html

2) The media ascribes new car smell to a single compound which is used to keep plastics soft and is also attributed to leaving a film on the inside of car windows (fogging). The compound is bis (2-ethylhexyl) phthalate.
Briefly explain why the media is likely wrong.

3) Australian researchers at CSIRO detected 30-40 volatile organic compounds (VOCs) in new car smell.
a) What analytical method did they use?
b) What are the symptoms of "negative sensory effects"?
c) In the study, what % of the VOCs remain in a new car after 6 months?....after 2 years?

4) New car smell can be purchased at auto supply stores as a "household" product. Manufacturers refuse to diviluge the contents, but a fragrance industry expert believes that it is a mixture of compounds respectively with three different chemical functions.
a) Name the three functions.
b) Referring to the chart of functional affinities for various GC stationary phases, select a single stationary phase for the separation of the 3 types of functions and rank the expected order of their relative retention times from lowest to highest.

5) From the article GC and the Coffee Crisis (pdf):
a) Draw a condensed structure for the compound found in the GC of coffee that causes it to taste sour after heat processing.
b) Name the three types of heterocylic compounds that are antioxidants which are found in coffee. Identify those that contain nitrogen and those that contain oxygen in their molecular formulas

GRADING Rubrik



Essential Oils / Steam Distillation / Extraction

Experimental
Introduction
Procedure / Instructions

IR spectra (clove oil components): major component ; minor component (~10%)
Post Lab Questions:

  1. Draw the structure of eugenol. Circle and label the chemical functions.
  2. On your IR: clearly identify and label the peaks that correspond to the functions cited above.
  3. Draw a separation scheme [organic layer (dichloromethane) vs. aqueous layer] that shows how eugenol was recovered from the distillate using NaOH and HCl. Use chemical equations and arrows to indicate electron movement for each step.
  4. Clove oil contains a minor component that has the formula C12H14O3. It produces eugenol and acetic acid upon acid catalyzed hydrolysis similar to methylsalicylate-salicylic acid. Draw a structure for the compound. Analyze your IR for its presence. Explain whether it is there or not from the IR data.
  5. Clove oil contains a structurally interesting isoprenoid in relatively small amounts. Its IUPAC name is (E)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene. What is the common name for this compound? Draw a structure for the compound. How many isoprene units are in the compound? Which class of terpene is it in?.... monoterpene, sesquiterpene, diterpene, sesterpene, triterpene, tetraterpene.


IR spectra (cumin extract): major component ; minor component
Structures of components
Post Lab Questions:

  1. Draw the respective structures of the major and inor components of cumin. Circle and label the chemical functions in each.
  2. From their respective IRs: clearly identify and label the peaks that correspond to the functions cited above.
  3. Briefly explain why the base-acid extractions that were done with eugenol and clove oil do not work to separate and purify cumin.

Answer questions 4, and 5 above for eugenol and clove oil:

Clove oil contains a minor component that has the formula C12H14O3. It produces eugenol and acetic acid upon acid catalyzed hydrolysis similar to methylsalicylate-salicylic acid. Draw a structure for the compound. Analyze your IR for its presence. Explain whether it is there or not from the IR data.

Clove oil contains a structurally interesting isoprenoid in relatively small amounts. Its IUPAC name is (E)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene. What is the common name for this compound? Draw a structure for the compound. How many isoprene units are in the compound? Which class of terpene is it in?.... monoterpene, sesquiterpene, diterpene, sesterpene, triterpene, tetraterpene.

Grading Rubrik


Identification of Terpenes

Terpenes/ UV Absorbtion Class
Terpenes/ UV Absorbtion pdf

Experimental
Unknown# ASSIGNMENTS   
     
Unknown DATA

UV Analysis Table
UV Analysis Table .pdf


Thin Layer Chromatography (TLC)

MOVIES:
Thin Layer Chromatography (TLC):
http://www.oid.ucla.edu/Webcast/chemistry/index.html
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
http://www.chem.ualberta.ca/%7Eorglabs/Techniques.html

Rf values: http://orgchem.colorado.edu/hndbksupport/TLC/TLCrf.html


Polarimetry / Stereochemistry/ Optical Resolution

Stereochemistry & Polarimetry

 

Part 1: Optical Rotation/ Carvone
Optical Rotation / Polarimetry: PART I
.pdf

Part 2: Chiral Molecules: Structure & Configuration
Optical Rotation: PART II
.pdf

Part 3: Enantiomeric Resolution of (+/-) Ibuprofen
Powerpoint Outline
.ppt (.pdf); Optical Rotation: PART III.pdf



Bromination of Stilbene

Prelab Worksheet

Experimental
Introduction
Procedure / Instructions

Bromination of Cinnamic Acid



SN1 , SN2 Reactions and Solvent Effects


Part 1: Individually, CPR- Calibrated Peer Review

Part 2: Team experimentation, analysis and presentations. (Handouts)
Procedures .pdf

Results Procedures A & B
Results Procedure C

Infection / Bacterial Resistance / Nucleophilic Displacement

Calvin Coolidge, Bacteria & Fate
"Shortly after the 1924 Republican Party convention, President Calvin Coolidge experienced a personal tragedy. Coolidge's younger son, Calvin, Jr., developed a blister from playing tennis on the White House courts. The blister became infected, and Calvin, Jr. died. After that Coolidge became even more withdrawn. He later said that "when he died, the power and glory of the Presidency went with him."

Reading:
Science-SN2-description.html
Science-SN2-article.html

Supplemental:
1) The "Roundabout" SN2 Mechanism- C&EN-08-description .pdf
2)
The "Roundabout" SN2 Mechanism- Science-08-article .pdf


Diels Alder Reactions / Molecular Modeling

Introduction pdf


Experimental Procedure
pdf

Molecular Modeling I pdf
Molecular Modeling II pdf

Post Lab Questions pdf


Lehman Experiment MINILAB #27: Diels Alder reaction of maleic anhydride and furan

University of Saskatchewan Alternative procedure .pdf
Molecular Modeling: Diels Alder Reactions (I) .pdf
Molecular Modeling: Diels Alder Reactions (II) .pdf



Colorful Grignard (14/20) (19/22)

Click on image for larger file

Experiment & Pre lab (pdf handouts)
Assigned Reagent

Vision Class
Vision pdf

Report & Post Lab Questions: Report Form pdf
Related Reading: Levi's Jeans

Lehman Experiment #32:Conjugated Diene / Diels Alder Reaction

Questions 1, 2, 3 & 5

Triphenylmethanol IR: KBr, nujpl mull respectively

http://www.aist.go.jp/RIODB/SDBS/ir/NIDA63390.gif
http://www.aist.go.jp/RIODB/SDBS/ir/NIDA64310.gif


On-line End-of-course Evaluation
Course ID : 13802
  Password: chem226