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 14

• 14.1 - Stability of Conjugated Dienes
 (1, 25, 51, 52a, 65)
  
• 14.2 - Electrophilic Additions to Conjugated Dienes
 (2, 3, 27, 54)
  
• 14.3 - Kinetic vs Thermodynamic Control of Reactions
 (5, 20, 28, 30, 60)
  
• 14.4 - The Diels-Alder Cycloaddition Reaction
 (21)
  
• 14.5 - Characteristics of the Diels-Alder Reaction
 (8, 9, 10, 22, 31, 33-37, 40, 41, 57)

Chapter 15

• 15.1 - Naming Aromatic Compounds (1-3, 18)
  
• 15.2 - Structure and Stability of Benzene
  
• 15.3 - Aromaticity and the Huckel 4n+2 Rule (5)
  
• 15.4 - Aromatic Ions (6, 7, 29, 31, 32, 34, 35)
  
• 15.5 - Aromatic Heterocycles: Pyridine and Pyrrole (9, 10, 37, 38, 43)
  
• 15.6 - Polycyclic Aromatic Compounds (12, 25)
  
• 15.7 - Spectroscopy of Aromatic Compounds (41, 47)

Chapter 16

• 16.1 - Electrophilic Aromatic Substitution Reactions: Bromination (1, 36)
  
• 16.2 - Other Aromatic Substitution (3, 4, 28)
  
• 16.3 - Alkylation and Acylation of Aromatic Rings (5-7, 40)
• 16.8 - Oxidation of Aromatic Compounds (18, 20)
  
• 16.9 - Reduction of Aromatic Compounds (53)
  
• 16.4 - Substituent Effects in Electrophilic Substitutions (8, 9, 10, 13, 31, 46-49, 52)
• 16.5 - Trisubstituted Benzenes: Additivity of Effects (14, 61)
  
• 24.8 - Reactions of Arylamines (Ch 24 #18)
  
• 16.6 - Nucleophilic Aromatic Substitution (16)
  
• 16.7 - Benzyne (17)
  
• 16.10 - Synthesis of Polysubstituted Benzenes (22, 23, 56, 57, 64, 74)

Chapter 17

• 17.1 - Naming Alcohols and Phenols (2, 37)
  
• 17.2 - Properties of Alcohols and Phenols (3, 4)
  
• 17.3 - Preparation of Alcohols: A Review (6a,c)
  
• 17.6 - Reactions of Alcohols (12, 30, 31, 45-47)
  
• 17.11 - Spectroscopy of Alcohols and Phenols (18, 51, 52, 75)

Chapter 18

• 18.1 - Names and Properties of Ether (1, 39)
• 18.2 - Preparing Ethers (3, 25, 43)
  
• 18.3 - Reactions of Ethers: Acidic Cleavage (7, 23, 24)
  
• 18.5 - Cyclic Ethers: Epoxides
  
• 18.6 - Reactions of Epoxides: Ring-Opening (12, 27, 28, 40)

Synthetic Transformations of Carbonyl Compounds (Ch 17, 19, 21)

• Preview of Carbonyl Chemistry: pg. 595-603
  
• 17.7 - Oxidation of Alcohols (14, 15, 72)
  
• 19.2 - Preparing Aldehydes and Ketones (3, 4)
  
• 19.3 - Oxidation of Aldehydes and Ketones
  
• 19.4 - Nucleophilic Addition Reactions of Aldehydes and Ketones
  
• 17.4 - Alcohols from Carbonyl Compounds: Reduction (7, 8, 29, 43)
  
• 17.5 - Alcohols from Carbonyl Compounds: Grignard Reaction (9, 42, 44)
  
• 19.7 - Nucleophilic Addition of Hydride and Grignard Reagents (31, 60)
  
• 21.3 - Conversion of Carboxylic Acids into Alcohols (Subsection)
  
• 21.4 - Conversion of Acid Chlorides into Alcohols (Subsection) (48a,b,c)
  
• 21.6 - Conversion of Esters into Alcohols (Subsection) (19, 34, 53a,b,e)
  
• 21.7 - Conversion of Amides into Amines (Subsection)
  
• 17.8 - Protection of Alcohols (Not on Exam 2)
  
• 19.13 - Conjugate Addition to a,b-unsaturated Aldehydes and Ketones (Organocopper Reaction Subsection) (22)
• 17.8 - Protection of Alcohols
  
• 19.13 - Conjugate Addition to a,b-unsaturated Aldehydes and Ketones (Organocopper Reaction Subsection) (22)

Chapter 19

• 19.1 - Naming Aldehydes and Ketones (1, 2, 54, 56, 57
  
• 19.5 - Nucleophilic Addition of H2O: Hydration (7)
  
• 19.6 - Nucleophilic Addition of HCN: Cyanohydrin Formation
  
• 19.8 - Nucleophilic Addition of Amines: Imine and Enamine Formation (10, 11, 34, 35)
  
• 19.9 - Nucleophilic Addition of Hydrazine: The Wolff-Kishner Reaction (13, 38)
  
• 19.10 - Nucleophilic Addition of Alcohols: Acetal Formation (32, 33)
  
• 19.11 - Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction (58, 61, 64)
  
• 19.14 - Spectroscopy of Aldehydes and Ketones (23, 24, 25)

Chapter 20

• 20.1 - Naming Carboxylic Acids and Nitriles (1, 2, 31, 34)
  
• 20.2 - Structure and Properties of Carboxylic Acids (3)
  
• 20.4 - Substituent Effects on Acidity (36, 37)
  
• 20.5 - Preparing Carboxylic Acids (21a, 23a, 44)
  
• 20.6 - Reactions of Carboxylic Acids: An Overview (11, 12, 43)
  
• 21.3 - Reactions of Carboxylic Acids (Ch 21 7, 32a,b, 33c)
  
• 20.7 - Chemistry of Nitriles (13, 14, 22a, 24a, 25a, 26, 45, 49, 65)

Chapter 21

• 21.1 - Naming Carboxylic Acid Derivatives (1a-g, 2, 45a-g)
  
• 21.2 - Nucleophilic Acyl Substitution Reactions (3, 4, 5, 31)
• 21.4 - Chemistry of Acid Halides (9, 11, 12)
  
• 21.5 - Chemistry of Acid Anhydrides (14, 15)
  
• 21.6 - Chemistry of Esters-Hydrolysis Section (54, 67)
  
• 21.7 - Chemistry of Amides-Hydrolysis Section
  
• 21.10 - Spectroscopy of Carboxylic Acid Derivatives (64, 66, 77, 78, 79)
  
• More Practice (52, 53, 73)

Chapter 22

• 22.1 - Keto-Enol Tautomerization
• 22.2 - Reactivity of Enols - Alpha Subsitution Reactions
• 22.3 - Alpha Halogenation of Aldehydes and Ketones
• 22.5 - Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation
• 22.6 - Reactivity of Enolate Ions
• 22.7 - Alkylation of Enolate Ions

Chapter 23

• 23.1 - The Aldol Reaction
• 23.2 - Carbonyl Condensation vs Alpha Substitutions
• 22.3 - Dehydration fo Aldol Products
• 23.4 - Using Aldol Reactions in Synthesis
• 23.5 - Mixed Aldol Reactions
• 23.6 - Intramolecular Aldol Reactions
• 23.7 - The Claisen Condensation Reaction
• 23.8 - Mixed Claisen Condensations
• 23.9 - The Dieckmann Cyclization
• 23.10 - The Michael Reaction
• 23.12 - The Robinson Annulation

Chapter 24

• 24.1 - Naming Amines (1, 2, 3)
  
• 24.2 - Structure and Properties of Amines (49)
  
• 24.3 - Basicity of Amines (4)
  
• 24.4 - Basicity of Aryl Amines (6)
  
• 24.6 - Synthesis of Amines (8, 9, 11, 30, 31, 53)
  
• 24.7 - Reactions of Amines (14, 61, 62, 64a,c, 68)
  
• 24.10 - Spectroscopy of Amines (25, 66)

Organometallic Compounds

• 10.6 - Reactions of Alkyl Halides: Grignard Reagents (9, 10, 26e,f,g, 42)
  
• 10.7 - Organometallic Coupling Reactions (11, 47, 50)

Chapter 25

• 25.1 - Classification of Carbohydrates
• 25.2 - Fischer Projections
• 25.3 - D,L Sugars
• 25.4 - Configuration of the Aldoses
• 25.5 - Cyclic Structure of Monosaccharides: Anomers
• 25.8 - Disaccharides
• 25.9 - Polysaccharides
• 25.10 - Some Other Important Carbohydrates