CHEM 227 - Organic Chemistry I

Fall 1998

Section 508 - 9:35 - 10:50 AM, Room 2102 Chemistry

Prof. Kenn Harding

Capsaicin - a colorless irritant phenolic amide (C₈H₂₇NO₃)obtained from various capsicum plants. It is the active ingredient in jalapenosand other 'hot peppers". Click here toaccess the pdb file (for viewing, rotation, etc. with RasMol or ChemscapeChimie). This structure was created using HyperChem.

First-day Handout

Exam Dates and Syllabus

Grades on the Web.

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Questions and Answers

Updated Sept. 14. 1998

Sources of Lecture Notes, Chapter Overviews, and Quizzes

The following are sources of lecture notes covering the topics covered in Chemistry 227.

On-Line Sources

Organic Chemistry Lecture Slides: McMurry Chapters 1 - 11- by P. R. Young, Univ. of Illinois - Chicago (requires Javascript enabled and Chemscape Chime plug-in)

Organic Chemistry Online by P. R. Young from Univ. of Illinois at Chicago.

Includes tutorials and interactive on-line quizzes. (requires Javascript enabled and Chemscape Chime plug-in)

Local Course Pack

Chem 227 - Sulikowski; Packet #260, Copy Corner ($12.10)

Announcements

General Tutorials Covering Topics for 227

Organic Chemistry Practice Problems - Michigan State University. Interactive quizzes color-coded for type of course.
Visualization Tools and Interactive Tutorials - University of Michigan. Topics covered: Acid-Base Equilibria, Cycloalkane Visualization, Nucleophilic Substitution Dry Laboratory, Organic Reaction Roadmap.

Reading and Problems assignments

Chapter One

Hybridization Handout

Ionic-Covalent Bonding Pictures

On-line Tutorials and Quizzes (also see On-line sources listed above)

Hybridization Tutor - by Daniel Dolata and Stavros Karatsoridis, Dept. of Chemistry, Ohio University
Visual Aids for Organic Chemistry from Colby College - Shockwave movies require Shockwave plug-in to your browser. Movies on "Orbitals" and on "Representing Compounds".
Structure and Bonding (includes on-line problem sets that check your answers!)

Chapter Two (with Helpful Hints for Chapter 2)

Reading Quiz for 9/8 will cover end of Chapter 1 and Chapter 2 through section 2.5

On-line Tutorials and Quizzes (also see Organic Chemistry lecture slides listed above)

Structure and Bonding (includes on-line problem sets that check your answers!) See Brief Reviews on: Resonance, and Acids and Bases. See On-line Problem Sets for: Unshared Pairs & Formal Charges, and Drawing Resonance Forms
Handout on "Lewis Dot Structures, Formal Charge, Resonance Structures & Arrows" - by Daniel Romo, Texas A&M University .

Chapter Three (with Helpful Hints)

Reading Quiz for 9/10 will cover end of Chapter 2 and Chapter 3 up to Section 3.8

Handouts relevant to Chapter 3 by Prof. Alan Shusterman at Reed College (requires Acrobat Reader)

On-line Tutorials and Quizzes (also see Organic Chemistry lecture slides listed above)

Structure and Bonding (includes on-line problem sets that check your answers!) See Brief Reviews on: Bonding in Organic Molecules, and On-line Problem Sets for: Conversion to and from Line Drawings.
Alkane Nomenclature Tutorial - By Daniel Dolata, Dept. of Chemistry, Ohio University
Complete Organic Nomenclature Tutorial - by Dave Woodcock, Dept. of Chemistry, Okanagan University (Versions for use with Chemscape Chime or with RasMol).
Cis-Trans Isomers on Cyclohexane Rings Tutorial (from University of Arizona)
Visual Aids for Organic Chemistry from Colby College - Shockwave movies require Shockwave plug-in to your browser. Movies on "Alkane Physical Properties" and "Cycloalkanes".

Chapter Four - Stereochemistry of Alkanes and Cycloalkanes

Helpful Hints for Chapter 4

Reading Quiz for 9/15 will cover only through Section 4.8

On-line Tutorials and Quizzes (also see Organic Chemistry lecture slides listed above)

Alkanes in Motion - a Quicktime movie clip from Journal of Chemical Education Software (software by J. H. Kim, Kongju National University, Korea)
Conformations of Alkanes and Cycloalkanes (QuickTime Animations from Univ. of Arizona)
Visual Aids for Organic Chemistry from Colby College - Shockwave movies require Shockwave plug-in to your browser. Movies on "What is a Dihedral Angle" and "Stereochemistry".
Conformations of Carbon Compounds (uses Chemscape Chime to allow viewing and manipulation of 3D structures) from Oberlin College
Conformations of Cycloalkanes - molecular models with optional highlighting of equatorial, axial, and flagpole hydrogens (by Abby Parrill at Michigan State Univ.).
Cycloalkane Conformations - By Daniel Dolata, Dept. of Chemistry, Ohio University (???)
Cybermodels by M. Schwartz at Florida State University.

Includes a "Cybermodel Viewer" to easily compare structures side-by-side. Requires Chemscape Chime.

Chapter Five- An Overview of Organic Reactions

Helpful Hints for Chapter 5

See Organic Chemistry lecture slides listed above

Animation of Addition of HBr to Propene (from Univ. of Texas; select Hydrogen Bromide Addition)

Chapter Six - Alkenes: Structure and Reactivity

Helpful Hints for Chapter 6

HBr Addition Pictures

On-line Tutorials and Quizzes (also see Organic Chemistry lecture slides listed above)

Tutorial on Alkene Stereoisomers and Nomenclature (from Univ. of Arizona)
Animation of Addition of HBr to Propene (from Univ. of Texas; select Hydrogen Bromide Addition)

Chapter Seven- Alkenes: Reactions and Synthesis

Helpful Hints for Chapter 7

Bromonium Ion Pictures

Bromohydrin Formation Pictures

On-line Tutorials and Quizzes (also see Organic Chemistry lecture slides listed above)

Structure and Bonding (includes on-line problem sets that check your answers!) Very good coverage of alkene reactions!

Chapter Eight- Alkynes

Helpful Hints for Chapter 8

Alkyne and Acetylide Anion Pictures

Chapter Nine- Stereochemistry

Enantiomers

Stereochemistry Handout for Chapter 9

Tutorials

Stereochemistry Tutorial 1 - Single Stereocenter (from Univ. of Arizona)

Stereochemistry Tutorial 2 - More than one Stereocenter (from Univ. of Arizona)

The Stereochem Game - a tutorial designed to provide drill in stereochemical concepts (from Univ. of Arizona)

Stereochemistry Online Page from Colby College - A great way to test your knowledge of stereochemistry.

A Roadmap for Classification of Isomers - by Daniel Romo at Texas A&M University

Visual Aids for Organic Chemistry from Colby College - Shockwave movies require Shockwave plug-in to your browser. Movie on "Computational Chemistry"

Stereochemistry Online Page at Colby College- Two types of exercises are provided. One involves the classification of a given molecule as either chiral, achiral, or meso. The other exercise involves the comparison of two molecules, and the determination of their relationship as enantiomers, diastereomers, constitutional isomers, non-isomers, or identical compounds. Requires Chemscape ChimeTM plug-in.

Chapter Ten - Alkyl Halides

Pictures - Radical Stability

Chapter Eleven- Reactions of Alkyl Halides

Pictures - S_N2 Substitution

- Substitution - Elimination

Animation of S_N2 Reaction and of Elimination Reaction (from Univ. of Texas)

Helpful Hints - Chapter 11

On-line Tutorials and Quizzes (also see Organic Chemistry lecture slides listed above)

Structure and Bonding (includes on-line problem sets that check your answers!)
Nucleophilic Substitution Dry Laboratory - including on-line Quiz (from Michigan State Univ.)
Tutorial on S_N2 Reactions - from Univ. of Arizona (includes visualization of structures along reaction coordinate)
Practice Questions for Nucleophilic Substitution (from Michigan State Univ.)