Use this list for the following: 1. Extra practice problem from the textbook (McMurry Organic Chemistry, 9th ed), 2. To see a preview of the topics as they will generally be covered in class. 3. To clearly find the beginning and end of each exam's material coverage. This list will be updated regularly to reflect any additional or removed content as we progress through the course.

Begin Exam 1 Material

Chapter 1
• 1-1: 
Atomic Structure: The Nucleus

• 1-2
: Atomic Structure: Orbitals

• 1-3
: Atomic Structure: Electron Configurations
 (1, 2)
• 1-4
: Development of Chemical Bonding Theory
 (3, 5, 6, 7, 26)
• 1-5
: Describing Chemical Bonds: Valence Bond Theory

• 1-6
: Hybrid Orbitals and the Structure of Methane

• 1-7
: Hybrid Orbitals and the Structure of Ethane
 (8)
• 1-8
: Hybrid Orbitals and the Structure of Ethylene
 (10, 11, 12, 27)
• 1-9
: Hybrid Orbitals and the Structure of Acetylene
 (13, 36, 46)
• 1-10
: Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur (14, 28, 38, 40, 50, 51)

• 1-11
: Describing Chemical Bonds: Molecular Orbital Theory

• 1-12
: Drawing Chemical Structures (15, 30, 33, 42, 43, 49)

Chapter 2
• 2-1: Polar Covalent Bonds:Electronegativity (1, 2, 3)
• 2-2: Polar Covalent Bonds: Dipole Moments (6, 32)
• 2-3: Formal Charges (7, 35)
• 2-4: Resonance
• 2-5: Rules for Resonance Forms
• 2-6: Drawing Resonance Forms (9, 10, 26, 38, 56)
• 2-7: Acids and Bases: The Bronsted-Lowry Definition (11, 55)
• 2-8: Acid and Base Strength (12, 13)
• 2-9: Predicting Acid-Base Reactions from pKa Values (14, 15, 44)
• 2-10: Organic Acids and Organic Bases (43)
• 2-11: Acids and Bases: The Lewis Definition (17, 24, 25, 27)
• Note: This chapter is a bit weak on a few topics so be sure to review your notes thoroughly, and do the posted problem set and resonance tutorial.

Chapter 3
• 3-1: Functional Groups (1, 22, 25, 53)
• 3-2: Alkanes and Alkane Isomers (4, 5, 29, 49)
• 3-3: Alkyl Groups (8, 9, 32)
• 3-4: Naming Alkanes (11, 12, 34, 35, 38,)
• 3-5: Properties of Alkanes - Skim this section. We will cover in detail later on.
• 3-6: Conformations of Ethane
• 3-7: Conformations of Other Alkanes (15, 16, 17, 43, 45, 51)

Chapter 4
• 4-1: Naming Cycloalkanes (1, 2b,d)
• 4-2: Cis-Trans Isomerism in Cycloalkanes (4, 5, 30, 54)
• 4-3: Stability of Cycloalkanes: Ring Strain (8, 9)
• 4-4: Conformations of Cycloalkanes (11)
• 4-5: Conformations of Cyclohexane
• 4-6: Axial and Equatorial Bonds in Cyclohexane (12, 13, 14, 34)
• 4-7: Conformations of Monosubstituted Cyclohexanes (15, 35, 36, 37, 38)
• 4-8 Conformations of Disubstituted Cyclohexanes (18, 42, 43, 45)

Chapter 5
• 5-1
: Enantiomers and the Tetrahedral Carbon

• 5-2
: The Reason for Handedness in Molecules: Chirality
 (2, 3, 36)
• 5-3: 
Optical Activity
 (6)
• 5-4
: Pasteur’s Discovery of Enantiomers
 (37)
• 5-5
: Sequence Rules for Specifying Configuration
 (7, 8, 9, 10, 11, 30, 43, 44, 45, 46, 49)
• 5-6
: Diastereomers
 (13, 14, 71, 72)
• 5-7: 
Meso Compounds
 (16, 17, 28, 32, 52, 54)
• 5-9
: A Review of Isomerism
 (21, 69)
• 5-10: 
Chirality at Nitrogen, Phosphorus, and Sulfur

• 5-12
: Chirality in Nature and Chiral Environments
• 25-2: Fischer Projections (25-2, 25-3, 25-4, 25-5, 25-41)

Chapter 6
• 6-1: Kinds of Organic Reactions
• 6-2: How Organic Reactions Occur: Mechanisms
• 6-3: Radical Reactions (Skip for now...we will come back to this in Ch 10)
• 6-4: Polar Reactions (4,5,30,33)
• 6-5: An Example of a Polar Reaction: Addition of HBr to Ethylene (6,7)
• 6-6: Using Curved Arrows in Polar Reaction Mechanisms (8,9,28,34,35,43,45,46,47)
• 6-7: Describing a Reaction: Equilibria, Rates, and Energy Changes (24)
• 6-8: Describing a Reaction: Bond Dissociation Energies
• 6-9: Describing a Reaction: Energy Diagrams and Transition States
• 6-10: Describing a Reaction: Intermediates (13, 17-23)
• 6-11: A Comparison Between Biological Reactions and Laboratory Reactions (we won't cover this, but you can read it for interest)
• Also work through the Practice Your Scientific Analysis and Reasoning I on pages 182-184. This is the type of passage and associated questions that you will see on exams such as the MCAT.

• 7-2 - Degree of Unsaturation
• 7-4 - CIs/Trans isomerism in alkenes

Chapter 7
• 7-1: Industrial Preparation and Use of Alkenes (Read for interest)
• 7-2: Calculating Degree of Unsaturation (1, 2, 3, 35)
• 7-3: Naming Alkenes (4, 5, 6, 37, 38a,b,d, 39, 40)
• 7-4: Cis-Trans Isomerism in Alkenes (9)
• 7-5: Alkene Stereochemistry and the E,Z Designation (13, 46)
• 7-6: Stability of Alkenes (15, 48)
• 7-7: Electrophilic Addition Reactions of Alkenes
• Read the blurb on page 204 titled "Writing Organic Reactions"
• 7-8: Orientation of Electrophilic Additions: Markovnikov's Rule (16, 17, 57a,b,d, 59)
• 7-9: Carbocation Structure and Stability (18, 54, 56, 60)
• 7-10: The Hammond Postulate (We won't cover this formally in lecture, but it is useful information)
• 7-11: Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements (21, 26a,b, 27a,b, 28, 30, 69)

Chapter 8
• 8-1
: Preparing Alkenes: A Preview of Elimination Reactions
 (1,2)
• 8-2: 
Halogenation of Alkenes: Addition of 
X2 (3,4,26)
• 8-3
: Halohydrins from Alkenes: Addition of X2/H2O 
(34,40)
• 8-5
: Hydration of Alkenes: Addition of 
by Hydroboration
 (9,10,28,46)
• 8-6
: Reduction of Alkenes: Hydrogenation
 (12)
• 8-7
: Oxidation of Alkenes: Epoxidation and Hydroxylation
 (13,14,29)
• 8-8
: Oxidation of Alkenes: Cleavage to Carbonyl Compounds
 (15,16,44a,b,c,51,52,65)
• 8-9
: Addition of Carbenes to Alkenes: Cyclopropane Synthesis (17
,42,43(all but e),48)
• 8-12: 
Reaction Stereochemistry: Addition of 
to an Achiral Alkene

• 8-13
: Reaction Stereochemistry: Addition of 
to a Chiral Alkene (20,21,32)

Chapter 9
• 9-1: Naming Alkynes (1,26,27)
• 9-2: Preparation of Alkynes: Elimination Reactions of Dihalides
• 9-3: Reactions of Alkynes: Addition of HX and X2 (3,18,19,28,57)
• 9-4: Hydration of Alkynes (4,5,6,20,21)
• 9-5: Reduction of Alkynes (8,22,30,31,32,33,46)
• 9-7: Alkyne Acidity: Formation of Acetylide Anions (9)
• 9-8: Alkylation of Acetylide Anions (10,11,24)
• 9-9: An Introduction to Organic Synthesis (12,13,35,36,37a-d,39,42)

Chapter 13
• 13-1: Nuclear Magnetic Resonance Spectroscopy
• 13-2: The Nature of NMR Absoprtions
• 13-3: The Chemical Shift (3)
• 13-4: Chemical Shifts in 1H NMR Spectroscopy (6,7)
• 13-5: Integrations of 1H NMR Absorptions: Proton Counting (8)
• 13-6: Spin-Spin Splitting in 1H NMR Spectra (9,10,11,38,39)
• 13-7: 1H NMR Spectroscopy and Proton Equivalence (12,34,40,41)
• 13-9: Uses of 1H NMR Spectroscopy (16,42,43)
• Solving Spectra: 44,45,52,53,54,55,58

Chapter 10
• 10-1: Names and Structures of Alkyl Halides (1,2 if you need review)
• 10-2: Radical Halogenation (3,17a,b,21)
• 10-3: Allylic Bromination (18a,34)
• 10-4: Stability of the Allyl Radical (6,7,18c,26c,27,30)

Chapter 11
• 11.1 - The Discovery of Nucleophilic Substitution Reactions (1)
• 11.2 - The SN2 Reaction (2,25)
• 11.3 - Characteristics of the SN2 Reaction (4,5,6,41,42,43,46,47,57)
• 11.4 - The SN1 Reaction (8,26,71)
• 11.5 - Characteristics of the SN1 Reaction (11,13,44,56)
• 11.7 - Elimination Reactions: Zaitsev's Rule (15,16)
• 11.8 - The E2 Reaction (17,28,50a-e)
• 11.9 - The E2 Reaction and Cyclohexane Conformation (19,66)
• 11.10 - The E1 and E1cB Reactions (52)
• 11.12 - A Summary of Reactivity: SN1, SN2, E1, E1cB, and E2 (20a,b,c, 30b,c,d, 58, 60, 67)