Organic Chemistry Outline and Chapter Objectives
Chemistry 416
Chapter 1: Electronic Structure and Covalent Bonding
1.1
1.2
1.3
1.4
1.5
1.6
1.7
1.8
1.9
1.10
1.11
1.12
1.13
The structure of the Atom
Objective 1: Define atomic number, mass number, Isotopes, atomic weight, and molecular weight.
Objective 2: Discuss the significance of radioactive Carbon-14 in nature.
How the Electrons in an Atom are Distributed
Objective 3: Define atomic orbitals.
Objective 4: Demonstrate how to map out electrons with the governing rules of electron
configurations.
Objective 5: Illustrate and identify the difference between valence and core electrons.
Ionic and Covalent Bonds
Objective 6: Define and illustrate ionic bonding.
Objective 7: Define and illustrate covalent bonding.
Objective 8: Demonstrate the difference between polar and nonpolar bonds.
How the Structure of a Compound is Represented
Objective 9: Draw Lewis structures for basic organic and inorganic compounds.
Objective 10: Define and demonstrate how to calculate formal charge.
Objective 11: Recognize the difference between Lewis, Kekule, Condensed, and Ball & Stick
structures.
(Review Molecular Geometries)
Atomic Orbitals
Objective 12: Draw s, p, and d orbitals.
(Review Quantum Numbers: Software – Orbital Viewer)
How Atoms Form Covalent Bonds
Objective 12: Define sigma bonds.
Objective 13: Define bond strength and bond length.
How Single Bonds are Formed in Organic Compounds
Objective: 14: Demonstrate how bonds form in methane and ethane using hybridization.
How a Double Bond is Formed: The Bonds in Ethene
Objective 15: Define a pi bond.
Objective 16: Conceptually illustrate how a pi bond forms in ethane.
How a Triple Bond is Formed: The Bonds in Ethyne
Objective 17: Examine and explain how a triple bond forms in ethyne.
Bonding in the Methyl Cation, the Methyl Radical, and the Methyl Anion
Objective 18: Define and illustrate the methyl cation, the methyl radical, and the methyl anion.
The Bonds in Water
Objective 19: Identify the important and unique properties of water. (Its polarity, hybridization,
molecular geometry, physical properties, and chemical properties.)
The Bonds in Ammonia and in the Ammonium Ion
Objective 20: Examine the characteristics of ammonia and the ammonium ion.
The Bond in a Hydrogen Halide
Objective 21: Examine the difference in bonds between the hydrogen halides.
1.14
Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles
Objective 22: Interconnect the relationships between
Chapter 2: Acids and Bases
2.1
An Introduction to Acids and Bases
Objective 1: Define and identify acids, bases, conjugate acids, and conjugate bases in a given
reaction.
2.2
pKa and pH
Objective 2: Relate pKa, pH, and the strength of an acid.
Objective 3: Mathematically calculate the pH and pKa of an acid solution.
2.3
Organic Acids and Bases
Objective 4: Graphically illustrate the acidity and basicity of several organic reactions.
2.4
How to Predict the Outcome of an Acid-Base Reaction
Objective 5: Qualitatively predict the products of an organic acid-base reaction.
2.5
How to Determine the Position of Equilibrium
Objective 6: Qualitatively identify equilibrium shift by examining pKa’s of the acid and conjugate acid.
2.6
How the Structure of an Acid Affects its pKa
Objective 7: Discuss the significance of structure and electronegativies in determining pKa for an
organic compound.
Objective 8: Examine and discuss acid strength of several organic compounds.
2.7
How pH Affects the Structure of an Organic Compound
Objective 9: Systematically predict the behavior of an acid by examining the pH of both the acid
compound and the solvent in a solution.
2.8
Buffer Solutions
Objective 10: Define and illustrate how a buffer solution works to minimize pH change upon the
introduction of an acid. (Case study: Blood’s Buffers)
2.9
Lewis Acids and Bases
Objective 11: Define Lewis acid and Lewis base and compare it to the traditional definitions of acids
and bases.
Chapter 3: An Introduction to Organic Compounds
3.1
How Alkyl Substituents Are Named
Objective 1: Identify and name the basic alkyl groups.
Objective 2: Identify the functional groups for alcohols, amines, and halides.
Objective 3: Distinguish between a primary , secondary, and tertiary carbons.
3.2
The Nomenclature of Alkanes
Objective 4: List and apply the IUPAC steps for systematically naming alkane structures.
3.3
The Nomenclature of Cycloalkanes
Objective 5: Identify cycloalkanes and systematically name.
3.4
The Nomenclature of Alkyl Halides
Objective 6: Systematically name alkane compounds that contain halides.
3.5
The Classification of Alkyl Halides, Alcohols, and Amines.
Objective 7: Distinguish the difference between primary, secondary, and tertiary class compounds.
3.6
The Structures of Alkyl Halides, Alcohols, Ethers, and Amines.
Objective 8: Examine, in detail (including hybridization and orbital geometry), the structures of alkyl
halides, alcohols, and amines.
3.7
The Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines.
Objective 9: Review the different types of intermolecular forces first discussed in inorganic chemistry.
Objective 10: Discuss how intermolecular forces influences boiling, melting point, and other physical
properties.
Objective 11: Examine the basic principles of solubility.
3.8
Rotation Occurs about Carbon-Carbon Single Bonds
Objective 12: Define and identify the different types of conformations.
Objective 13: Examine the 3-dimensional spatial arrangement of alkane structures. (Specifically
around the carbon-carbon single bond.)
3.9
Some Cycloalkanes Have Angle Strain
Objective 14: Define angle strain and identify its affect on bond strength.
3.10 Conformers of Cyclohexanes
Objective 15: Identify and examine the boat and chair conformations of cyclohexane.
Objective 16: Define and label axial and equatorial bonds around a cycloalkane.
3.11 Conformers of Monosubstituted Cyclohexanes
Objective 17: Discuss how the addition of a substituted group affects conformation strain.
3.12 Conformers of Disubstituted Cyclohexanes
Objective 18: Define cis-trans configurations of cycloalkanes and ring flip.
Objective 19: Examine energetically the ring flip of several disubstituted cycloalkanes.
3.13 Fused Cyclohexane Rings
Objective 20: Identify and examine fused cyclohexane rings.
Chapter 4: Alkenes-Structure, Nomenclature, Stability, and an Introduction to Reactivity.
4.1
Molecular Formulas
Objective 1: Define and identify saturated and unsaturated hydrocarbons.
4.2
The Nomenclature of Alkenes
Objective 2: List and apply the IUPAC steps for systematically naming alkene hydrocarbons.
4.3
The Structure of Alkenes
Objective 3: Examine the structure of alkenes.
4.4
Alkenes Can Have Cis-Trans Isomers
Objective 4: Determine when Cis-Trans labels can be applied to an alkene compound.
4.5
Naming Alkenes Using the E,Z System
Objective 5: List the steps and apply the E,Z system to naming alkenes that have multiple geometric
isomers.
4.6
The Relative Stabilities of Alkenes
Objective 6: Examine the energetic stability of the structures of an alkene isomer.
4.7
How Alkenes React
Objective 7: Define functional group, electrophile, and nucleophile.
Objective 8: Discuss how mechanisms are used to describe, in detail, a chemical reaction.
Objective 9: Use curved arrows to illustrate the process of bonds breaking and forming in a chemical
reaction.
4.8
A Reaction Coordinate Diagram Describes the Energy Changes that Take Place During a Reaction.
Objective 10: Define and give examples of a transition state.
Objective 11: Illustrate the fluctuation in energy during a reaction with a reaction coordinate
diagram.
Objective 12: Use the concepts of Gibs free energy to examine qualitatively the favorability of a
reaction.
Objective 13: Identify the factors that determine the rate of reaction.
Chapter 9: Substitution and Elimination Reactions of Alkyl Halides
9.1
9.2
9.3
9.4
9.5
9.6
9.7
9.8
9.9
9.10
9.11
9.12
9.13
How Alkyl Halides React
Objective 9.1: Define and identify substitution and elimination reaction.
Objective 9.2: Give a qualitative explanation to why alkyl halides react.
The mechanism of an Sn2 Reaction
Objective 9.3: Discuss how concentration of a reagent may or may not effect reaction rate.
Objective 9.4: Define molecular rates and identify the three pieces of experimental evidence that
supports the multistep mechanism.
Objective 9.5: Define steric effects and steric hindrance and it’s effect on reactivity.
Factors That Affect SN2 Reactions
Objective 9.6: Illustrate the two factors affecting SN2 reaction rates; leaving group and the
nucleophile.
Objective 9.7: Illustrate the mechanism for an SN1 reaction.
Objective 9.8: Examine the energy coordinate diagram for an SN1 reaction.
Objective 9.9: Examine and compare factors affecting SN1 reactions.
Objective 9.10: Compare and examine the contrast and similarities between SN2 and SN1 reactions.
(Using table 9.3)
Objective 9.11: Examine elimination reactions of alkyl halides.
Objective 9.12: Illustrate the mechanisms for E1 and E2 reactions.
Objective 9.13: Identify the products of elimination reactions and examine the driving force behind
them.
Objective 9:14: Compare and contrast E2 and E1 reactions.
Objective 9.15: Identify and discuss the rate law expressions for both SN2/E2 and SN1/E1 pairings.
Objective 9.16: Predict whether a reaction with an alkyl halide will undergo SN1, SN2, E1, or E2 type
of reaction.
Objective 9.17: Examine the impact of the solvent on substitution and elimination reactions.
Objective 9.18: Demonstrate how substitution reactions can be used to synthesize organic
compounds.
Chapter 10: Reactions of Alcohols, Amines, Ethers, and Epoxides
10.1
10.2
10.3
10.4
10.5
10.6
10.7
10.8
Objective 10.1: Use IUPAC nomenclature rules to name alcohols.
Objective 10.2: Examine and demonstrate substitution reactions involving alcohols.
Objective 10.3: Examine and demonstrate the dehydration of alcohols.
Objective 10.4: Examine, demonstrate, and predict reactions involving the oxidation of
alcohols to form ketones and aldehydes.
Objective 10.5: Discuss and illustrate why amines do not undergo substitution or elimination
reactions.
Objective 10.6: Use IUPAC nomenclature rules to name ethers.
Objective 10.7: Examine and illustrate nucleophilic substitution reactions of ethers.
Objective 10.8: Illustrate and predict reactions of epoxides forming a variety of organic
compounds.
Objective 10.9: Examine and use correct reactants to form epoxides.