CHEM 2260 - Organic Chemistry 1

Credit Hours: 4.00

Objectives: During the course, students will:

1. Describe chemical bonding using the Lewis and Valence Bonding Theories.
2. Draw representations of organic compounds using various structural formulas.
3. Draw and predict the validity of resonance forms.
4. Predict the shape and polarity of simple molecules and molecular fragments.
5. Use acid/base theories to predict the directionality of chemical reactions.

Outcome 2: Upon completion of this course, students will be able to demonstrate a working knowledge of saturated hydrocarbons
(alkanes and cycloalkanes).

Objectives: During the course, students will:

1. Classify hydrocarbons as aliphatic or aromatic.
2. Identify aliphatic hydrocarbons as alkanes, alkenes or alkynes.
3. Describe bonding in alkenes and cycloalkanes using sp3 hybridization.
4. Provide acceptable IUPAC names and structures to alkanes and cycloalkanes.
5. Distinguish between primary (1º), secondary (2º) and tertiary (3º) carbon atoms.
6. Explain the physical properties of alkanes and cycloalkanes.
7. Use heats of combustion to measure the stability of isomeric alkanes and cycloalkanes.

Outcome 3: Upon successful completion of this course, the student will be able to discuss the relative stability of alkanes and cycloalkanes using conformational analysis.

Objectives: During the course, students will:

1. Distinguish between eclipsed and staggered conformations.
2. Draw molecules using sawhorse and Newman projections.
3. Relate potential energy diagrams to torsional and steric strain.
4. Identify the shapes of cycloalkanes in terms of angle strain.
5. Draw and identify axial and equatorial substituents on a cyclohexane ring.
6. Identify the most stable conformation of mono- and disubstituted cyclohexanes.
7. Provide acceptable IUPAC names and structures to polycyclic ring systems.
8. Identify and draw common heterocyclic compounds.

Outcome 4: Upon successful completion of this course, the student will be able to demonstrate a working knowledge of compounds containing alcohol and alkyl halide functionalities.

Objectives: During the course, students will:

1. Identify and name various organic functional groups.
2. Provide acceptable IUPAC names and structures for alcohols and alkyl halides.
3. Distinguish between primary (1º), secondary (2º) and tertiary (3º) alcohols and alkyl halides.
4. Discuss the physical and chemical properties of alcohols and alkyl halides in terms of their intermolecular forces.
5. Describe the synthesis of alkyl halides from alcohols and hydrogen halides.
6. Draw and explain each step involved in SN1 and SN2 reaction mechanisms.
7. Relate carbocation stability to the rates of applicable substitution reactions.
8. Relate alcohol structure to the rates of applicable substitution reactions.
9. Describe the synthesis of alkyl halides from alcohols and specialized inorganic reagents.
10. Discuss the free radical halogenation of alkanes and cycloalkanes, using light or heat, in terms of the stability of the free radicals generated.

Outcome 5: Upon successful completion of this course, the student will be able to demonstrate a working knowledge of the synthesis of compounds containing alkene and cycloalkene functionalities.

Objectives: During the course, students will:

1. Provide acceptable IUPAC names and structures for alkenes and cycloalkenes.
2. Assign stereochemical descriptors to alkene and cycloalkene names using the cis/trans or E/Z systems where appropriate.
3. Use the sp2 hybridization scheme to describe the structure and bonding in alkenes and cycloalkenes.
4. Explain the stability of substituted alkenes and cycloalkenes.
5. Describe the synthesis of alkenes and cycloalkenes through a variety of elimination reactions.
6. Use Zaitsev’s rule to predict the regioselectivity of elimination reactions.
7. Write and explain each step of E1 and E2 reaction mechanisms.
8. Account for unusual alkene products through alternate rearrangement pathways.
9. Describe anti elimination in E2 reactions.

Outcome 6: Upon successful completion of this course, the student will be able to demonstrate a working knowledge of the reactions of compounds containing alkene and cycloalkene functionalities.

Objectives: During the course, students will:

1. Use heats of hydrogenation to predict the stability of substituted alkenes and cycloalkenes.
2. Account for the stereochemistry of alkene hydrogenation.
3. Predict the products of electrophilic addition reactions of alkenes and cycloalkenes.
4. Explain the regioselectivity of addition reactions using Markovnikov’s rule.
5. Provide a mechanistic explanation for Markovnikov’s rule.
6. Justify certain addition products based on carbocation rearrangements.
7. Explain the free radical addition products of alkenes and cycloalkenes.
8. Account for the stereochemistry of hydroboration/oxidation reactions of alkenes and cycloalkenes.
9. Use mechanisms to explain the stereochemistry of addition products to alkenes and cycloalkenes.
10. Use retrosynthetic analysis to devise synthetic pathways starting from alkenes and cycloalkenes.
11. Explain the formation of polymers starting from alkene monomers.

Outcome 7: Upon successful completion of this course, the student will be able to develop a feeling for molecules as three-dimensional objects.

Objectives: During the course, students will:

1. Distinguish between chiral and achiral molecules.
2. Describe the relationship between pairs of molecules (identical, constitutional isomers, enantiomers, diastereomers, etc…).
3. Locate symmetry elements within a compound.
4. Identify if a molecule is optically active.
5. Provide the proper R/S stereochemical descriptors to the names of chiral molecules.
6. Represent the three dimensional arrangement of a molecule’s atoms using Fischer projections.
7. Describe reactions that produce one (or more) chiral centers.
8. Describe the resolution of stereoisomers.

Outcome 8: Upon successful completion of this course, the student will be able to demonstrate a working knowledge of nucleophilic substitution reactions.

Objectives: During the course, students will:

1. Differentiate between nucleophiles and electrophiles.
2. Describe the usefulness of the halides as leaving groups.
3. Predict the stereochemistry of the products of an SN1 or SN2reaction.
4. Relate electrophile structure to the rates of SN2 reactions.
5. Predict the nucleophilicity of nucleophiles.
6. Discuss solvent effects on the rate of substitution reactions.
7. Analyze the competition between substitution and elimination reactions.
8. Describe leaving group transformation reactions.

Outcome 9: Upon successful completion of this course, the student will be able to demonstrate a working knowledge of the preparation and reactions of compounds containing alkyne and cycloalkyne functionalities.

Objectives: During the course, students will:

1. Provide acceptable IUPAC names and structures for alkynes and cycloalkynes.
2. Use the sp hybridization scheme to describe the structure and bonding in alkynes and cycloalkynes.
3. Explain the unusual acidity of terminal alkynes.
4. Describe methods to prepare alkynes and cycloalkynes.
5. Illustrate common reactions of alkynes and cycloalkynes.

Outcome 10: Upon successful completion of this course, the student will be able to demonstrate a working knowledge of the preparation and reactions of compounds containing polyenes and allylic functionalities.

Objectives: During the course, students will:

1. Identify various conjugated systems.
2. Identify allylic and vinylic substituents.
3. Rationalize the increased stability of allylic systems.
4. Predict the product distribution of allylic systems.
5. Illustrate common reactions of conjugated systems.
6. Differentiate between conjugated, isolated and cumulated dienes.
7. Describe methods to prepare dienes.
8. Predict the products of conjugate and direct addition reactions of dienes.

Outcome 11: Upon successful completion of this course, the student will be able to demonstrate a working knowledge of the basic properties and reactions of arenes.

Objectives: During the course, students will:

1. Describe what is meant by aromatic stability and how it applies to compounds containing a benzene unit.
2. Illustrate the thought process behind the discovery of benzene’s structure.
3. Use resonance pictures to describe the structure of benzene.
4. Provide acceptable IUPAC names for mono- and polysubstituted derivatives of benzene.
5. Draw the most stable resonance contributor for polycyclic aromatic hydrocarbons.
6. Compare the physical properties of aromatic and aliphatic hydrocarbons.

1. Fundamentals of Organic Structure
   1. Lewis and Valence Bonding Theory
   2. Acid/Base Theory
   3. Nomenclature of Alkanes
   4. Structure of Alkanes
   5. Conformational Analysis of Alkanes
2. Fundamentals of Organic Reactivity
   1. Substitution Reactions in Alcohols and Alkyl Halides
   2. The Mechanisms of SN1 and SN2 Reaction
   3. Elimination Reactions of Alcohols and Alkyl Halides
   4. The Mechanisms of E1 and E2 Reactions
   5. Addition Reactions of Alkenes and Alkynes
   6. The Mechanism of Addition Reactions
   7. Stereochemistry in Organic Reactions
   8. Introduction to Retro-Synthetic Analysis and Organic Synthesis
3. Introduction to Conjugation and Aromaticity
   1. Allylic Systems
   2. Dienes
   3. Bonding in Conjugated Dienes
   4. Addition to Conjugated Dienes
   5. The Diels-Alder Reaction
   6. Introduction to Molecular Orbital Theory
   7. The Stability of Benzene
   8. The Resonance Theory of Benzene
   9. The MO Theory of Benzene
   10. Nomenclature of Benzene Derivatives
   11. Hückel’s Rule
   12. The Frost Circle
   13. Aromaticity in Compounds Other Than Benze