Gustavus Adolphus
College
Minnesota Board of Teaching
Program Approval 2006

CHE 141 - Organic Chemistry I

CHE-141

Organic Chemistry I

Spring 2005

Gustavus Adolphus College

 

Prof. Scott Bur

Office: 303B, Nobel Hall                                                               Website: gustavus.edu/~sbur

Telephone: 933-7038

Email: sbur@gustavus.edu

 

Textbook:            Organic Chemistry, Brown, Foote and Iverson; 4th edition (2005)

                        OPTIONAL: Student Study Guide and Soluions Manual for Organic Chemistry, Iverson & Iverson, 4th Edition, (2005)

 

Supplies :  Molecular models.  These are not a requirement, but I strongly urge you to purchase a set.  You may use the model sets during the exams.  I still have (and use) the set I bought for Organic I.

 

Classroom:                        8:00 am - NHS 201

                        11:30 am Wallenburg auditorium, Nobel Hall

 

Office Hours:  My scheduled office hours are the following, or by appointment;

Mon - Tue - Thu:  9:00 to10:00 am

 

Homework:

I will give you a selection of homework problems out of the textbook to do as we cover each topic in class.  You should try to work the assigned problems on a regular basis, rather than trying to do them all right before the exam.  Any questions that you have with regard to the homework problems are welcome as topics for discussion during or outside of class.  These homework problems will not be collected for a grade.  As the exams will reflect the concepts and skills that the homework will develop, however, your grades will ultimately reflect your performance on these homework problems.

At the beginning of each week, you will be given an additional set of homework problems that will be collected for a grade each Friday on which there is not an exam.  These assignments must be turned in at the end of class to be graded.  Because chemistry is a collaborative science, you are encouraged to work with others as you are trying to work both the textbook problems and the homework sets.  It is, however, important to distinguish between working with someone, receiving help from someone, and copying someone else's work.  Obviously, copying someone else's work is unacceptable, and you will receive a zero for assignments.

 

 

 

Quizes:

            During the semester, I will give short quizzes at the end of class each Friday on which there is not an exam.  These will be brief, short-answer or multiple-choice questions to test your basic understanding of the topics covered during the week.  Makeup quizzes will not be given under any circumstances!  The combined average of homework and quizzes can be used to replace your lowest hourly exam score.

 

Exams:

            There will be four 1-hour exams that will consist of short answer and/or multiple-choice questions.  In addition to asking you the be able to recall facts and principles from lectures and textbook readings, you will be asked to extend the principles you learned to new situations and to offer explanations of the behavior of compounds with which you are not familiar.  Although the exams will not be formally comprehensive, each new concept builds upon previous material.  So you will need to know material from earlier units even if they are not tested directly.  The average of your homework and quiz scores can be used to replace your lowest test score.  Test dates are as follows:  February 25; March 18; April 15; and May 6.  The final exam will be comprehensive, and it is scheduled for Tuesday May, 21 from 8:00 am to 10:00 am in NHS AUD.

 


Course Coverage

            In first semester organic chemistry (the chemistry of carbon-containing compounds), we will learn the language and many of the principles governing organic chemistry.  We will study molecular structures, nomenclature, reactions, and reaction mechanisms of alkanes, alkenes, haloalkanes, alcohols, and ethers.  We will also learn about some of the analytical tools used for structure identification.

The schedule below gives a tentative outline of the topics we will study.  Note that this schedule can change depending on how much time we need to spend on a subject.

Topic

Reading

Lectures

Bonding and Structure

Chapter 1

Feb 7 - 11

            Electronic Structure

            Lewis Structures

            Functional Groups

            Molecular Geometry

            Polar and Non-polar Molecules

            Resonance Theory

            Quantum Mechanics

            Molecular Orbital and Valence Bond Theory of Bonding

Alkanes and Cycloalkanes

Chapter 2

Feb 14 - 18

            Structure

            Constitutional Isomerism

            Nomenclature

            Cycloalkanes

            IUPAC Nomenclature

            Conformations of Alkanes and Cycloalkanes

            Cis, Trans Isomerism in Cycloalkanes and Bicycloalkanes

            Physical Properties

            Reaction of Alkanes

Chirality

Chapter 3

Feb 21 - 28

            Stereoisomerism

            Chirality

            Naming Chiral Centers

            Molecules with multiple stereocenters

            Properties of Stereoisomers

            Optical Activity

            Resolution of Enantiomers

            Chirality and Biological Activity

EXAM I

Ch 1, 2, 3

Feb 25 (Friday)

Acids and Bases

Chapter 4

March 2-4

            Brønsted-Lowry Acids and Bases

            Dissociate Constants, pKa, and Relative Strengths of Acids and Bases

            Position of Equilibrium in Acid-Base Reactions

            Molecular Structure and Acidity

            Lewis Acids and Bases


 

Alkenes

Chapters 5

March 7 - 1

            Structure

            Nomenclature

            Physical Properties

            Natural Products: Terpenes

Alkenes II

Chapter 6

March 14 - 17

            Reactions

                        Electrophilic Additions

                        Hydroboration / Oxidation

                        Oxidation

                        Reduction

            Reactants or Products with Chiral Centers

EXAM II

Ch 4, 5, 6

March 18

Haloalkanes

Chapter 8

March 21 - 24, April 4

            Structure

            Nomenclature

            Physical Properties

            Preparation by Radical Halogenation

            Mechanism of Radical Halogenation

                        Hammond's Postulate

                        Stability of Radicals

            Allylic Halogenation

            Radical Addition of HBr

Spring Break (March 25 - April 3)

Nucleophilic Substitution

Chapter 9

April 6 - 11

            Bimolecular or Unimolecular Rate Determining Step

            Solvent Effects

            Evidence for SN2 and SN1 mechanisms

            Analysis of Nucleophilic Substitutions

                        Nucleophilicity

                        Carbocation Stability

                        Leaving Group

                        Structure of Electrophile

b-Elimination

Chapter 9

April 13 - 14

            Evidence for E2 and E1 mechanisms

            Substitution vs Elimination

            Phase Transfer Catalysis

            Neighboring Group Participation

EXAM III

Ch 8, 9

April 15

Infrared (IR) spectroscopy

Chapter 12

April 18 - 21

            Electromagnetic Radiation

            Molecular Spectroscopy

            Infrared Spectroscopy

            Interpreting IR Spectra


 

NMR Spectroscopy

Chapter 13

April 22 - 29

            Nuclear Spin States

            Orientation of Spins in a Magnetic Field

            Nuclear Magnetic Resonance

            Equivalent Hydrogens

            Integration

            Chemical Shift

            Signal Splitting

            Carbon-13 NMR Spectroscopy

            Interpretation of NMR Spectra

            Solving Structures from NMR and IR spectra

Alcohols and Thiols

Chapter 10

May 2 - 6

            Structure and Nomenclature

            Physical Properties

            Acid Base Chemistry of Alcohols

            Reactions of Alcohols

                        Conversion to Alkyl Halides and Sulfonate Esters

                        Acid Catalyzed Dehydration

                        Pinacol Rearrangement

                        Ocidation

            Thiols

EXAM IV

Ch 10, 12, 13

May 6

 


Laboratory

We will use the following text books:

 

Modern Projects and Experiments in Organic Chemistry: Miniscale and Standard Taper Microscale, Mohrig et al. (2003). 

 

Techniques in Organic Chemistry, Mohrig et al. (2003).

 

Laboratory Coverage

Experiment

Date

Lab

 

2/7 - 2/10

Check in

Model Building

1

2/14 - 2/24

White Solids

Goal: Understand the importance of physical properties, such as melting point and polarity, and how to measure them.  Identify an unknown compound using physical properties

2

2/28 - 3/17

Ester Hydrolysis

Goal: Hydrolyze an unknown ester and purify the hydrolysis products.  Identify the products based upon melting point, boiling point, and/or refractive index, then indentify the unknown ester.

3

3/21 - 3/24

Limonene

Goal: Isolate the essential oils from orange peel and determine the optical rotation of the oil.

4

4/4 - 4/7

Stereochemistry of Bromination

Goal: Purify the product of bromine addition to cinnamic acid and determine the relative stereochemistry of the product.  Determine the stereochemical course of bromination...cis or trans?

5

4/11 - 4/14

Oxidation - Reduction

Goal: Oxidize t-butylcyclohexanol to the corresponding ketone, then reduce the ketone to the alcohol.  Examine the stereoselectivity of the reduction using NMR and Gas Chormatography.

6

4/25 -4/28

Qualitative Analysis and Spectroscopy

Goal:  Conduct chemical tests to determine the functional groups present in an unknown compound and determine the structure using NMR spectroscopy.

 

5/9 - 5/12

Checkout