Course Outline: Organic Chemistry I (CHM270)

Credits: 5

Contact Hours:

Lecture: 3

Lab: 4

NOTE on Laboratory: Both Lecture and Laboratory must be taken simultaneously; separate grades will not be given for either. Students must pass the laboratory section to receive a passing grade in the entire course.

Semesters Offered: Fall, Spring, & Summer

Prerequisites: CHM 153 or equivalent

Catalog Course Description:

A study of the compounds of carbon involving a thorough integration of fact and theory and emphasizing the relationships between structures, properties, mechanisms, and reactions. This course, intended for science and pre-professional majors, covers topics such as bonding and structure, alkanes, alkenes, alkynes, stereochemistry, alkyl halides, and alcohols.

Required Course for: Bioscience; Certificate for Health Professions

Elective Course for: Science, Technology, & Society; Liberal Arts & Sciences

Course Texts:

Organic Chemistry (Wade, 9^th Edition, Pearson)

Organic Chemistry Laboratory Manual CHM 270 (ed. Michael DeCastro, FSC Chemistry Dept.)

Other Required Course Materials

Calculator, laboratory coat and safety glasses or goggles.

Course Learning Objectives:

I. Introduction

Review of structural theory, atomic orbitals, ionic bonding, covalent bonding, molecular geometry, electronegativity, molecular orbitals and acid-base theories.

At the end of this section, the student should be able to:

1. Predict the number of valence-shell electrons of an element.
2. Predict the electronegativity of an element.
3. Draw Lewis electron dot structures for simple compounds.
4. Draw line-bond structures for compounds.
5. Predict and describe the hybridization of bonds in organic compounds.
6. Draw organic structures with correct three- dimensional geometry.
7. Identify bonds in a molecule as ionic or covalent.
8. Predict the polarity of a bond.
9. Distinguish between a sigma and a Pi molecular orbital.
10. Identify the conjugate acid-base pairs in Bronsted Lowry acid-base reactions.
11. Identify Lewis acids and bases.
12. Be familiar with Kekule and Skeletal Structures.

II. Alkanes

Structures, nomenclature, physical properties, preparations, chemical eactions, mechanisms and free radical intermediates.

At the end of this section, the student should be able to:

1. Draw all isomers of a given alkane molecular formula.
2. Name alkanes by the IUPAC system.
3. Draw structures of alkanes corresponding to a given IUPAC name.
4. Identify carbon atoms as primary, secondary, tertiary or quarternarly.
5. Identify and draw structures of alkyl groups.
6. List methods of preparing alkanes.
7. List reactions of alkanes.
8. Write a mechanism for the halogenation of an alkane.
9. Apply the free radical mechanism to other compounds.

III. Alkenes

Structure, nomenclature, physical properties, preparations, chemical reactions, mechanisms and carbocation intermediates.

At the end of this section, the student should be able to:

1. Name alkenes by the IUPAC system.
2. Draw structures of alkenes corresponding to a given IUPAC name.
3. Draw all the isomers of a given alkene molecule.
4. Draw a molecular orbital picture of an alkene.
5. Differentiate between cis and trans isomers.
6. Write chemical equations for the preparation of alkenes.
7. Write chemical equations for the reactions of alkenes.
8. Write a general mechanism for addition reactions of alkenes.
9. Explain Markovnikov’s Rule and “the peroxide effect”.
10. Write a mechanism for Markovnikov’s addition reactions.
11. Write a mechanism for anti-Markovnikov’s addition reaction.
12. Explain how a carbanion forms.

IV. Alkynes and Dienes

Structure, nomenclature, physical properties, preparations, chemical reactions, and mechanisms.

At the end of this section, the student should be able to:

1. Name alkynes and dienes by the IUPAC system.
2. Draw structures of alkynes and dienes corresponding to a given IUPAC name.
3. Draw all isomers of a given alkyne molecule.
4. Draw the molecular orbital picture of a typical alkyne and diene.
5. Explain resonance and resonance energy concepts.
6. Write chemical equations for the preparation of alkynes and dienes.
7. Write chemical equations for the reactions of alkynes and dienes.
8. Explain the principle behind 1, 4 – addition reactions of dienes.
9. Propose a mechanism for 1, 4 – addition reactions.
10. Explain keto-enol tautomerization.

V. Cyclic Aliphatic Hydrocarbons

Structure, nomenclature, physical properties, preparations, stereochemistry, chemical reactions, mechanisms and carbene intermediates.

At the end of this section, the student should be able to:

1. Explain the reactivity of small rings.
2. Define Baeyer, Transannular and Pitzer strains.
3. Write chemical equations for the formation of cycloalkanes.
4. Explain how carbenes are formed.
5. Explain carbene insertion reaction mechanism.
6. Describe the three dimensional shapes of cycloalkanes of five carbon atoms or less.
7. Describe the three dimensional shapes of cycloalkanes of six carbon atoms or greater.
8. Locate axial and equitorial positions on cyclohexane.
9. Identify cis and trans positions on a cyclohexane ring.
10. Write chemical equations for the formation of cycloalkenes and cycloalkynes.

VI. Stereochemistry

Isomer number, optical activity, specific rotation, enantiomerism, chiral carbon, racemic modification, projections, Cahn- Ingold-Prelog (r,s) nomenclature, stereoisomers, and stereospecific reactions.

At the end of this section, the student should be able to:

1. Explain the meaning of isomer number.
2. Explain the causes of optical activity.
3. Calculate the specific rotation of a solution.
4. Decide whether objects are chiral.
5. Locate stereocenters in molecules.
6. Draw the enantiomer of a given chiral compound.
7. Draw the diastereoisomer of a given chiral compound.
8. Apply Van’t Hoff’s Rule.
9. Identify racemic modifications.
10. Draw chiral molecules in Newman and Sawhorse projections.
11. Assign priorities to substituents around a carbon stereocenter.
12. Assign R, S configurations to stereocenters.
13. Decide if a stereoisomer is a meso compound.
14. Predict the stereochemistry of reaction products.

VII. Alcohols

Structure, nomenclature, physical properties, preparation, chemical reactions, mechanisms and synthesis.

At the end of this section, the student should be able to:

1. Give the general structure of an alcohol.
2. Name alcohols by the IUPAC system.
3. Draw structures corresponding to IUPAC names of given alcohols.
4. Predict relative acidities of molecules.
5. Synthesize alcohols.
6. Predict products of reactions involving alcohols.
7. Formulate the mechanisms of reactions involving alcohols.
8. Explain how the Lucas test is used to distinguish between primary, secondary and tertiary alcohols.
9. Explain the anti-Markovnikov’s addition of water via hydroboration.

Laboratory Schedule

Experiment # Title

1. Melting Points
2. Separation of a Three Component Mixture
3. TLC Analysis of Analgesic Drugs
4. Distillation of a Water-Methanol Mixture
5. Preparation of Banana Oil (Isoamyl Acetate)
6. Isolation of Caffeine from Tea
7. Preparation of Acetyl Salicylic Acid
8. Steam Distillation of Oil of Cloves
9. Separation of Unknowns by Gas Chromatography
   Identification by Index of Refraction
10. Introduction to NMR
11. Synthesis of n-Butyl Bromide
12. Oxidation/Reduction of Borneol/Camphor