CHEM 2425 Course Objectives
Section numbers reference
"Organic Chemistry" Wade, 4th ed.
L = lab
O = optional
X = omit
B = brief overview
8. Reactions of Alkenes
8-6 Alkoxymercuration-Demercuration
8-7 Hydroboration of
Alkenes
8-13 Acid-Catalyzed opening of Epoxides
17. Reactions of Aromatic Compounds
17.15 Reactions of Phenols
12. Infrared Spectroscopy
and Mass Spectrometry
L 12-2 The Electromagnetic
Spectrum
L 12-3 The Infrared Region
L 12-4 Molecular Vibrations
L 12-5 IR-Active and
IR-Inactive Vibrations
L 12-6 Measurement of the IR
Spectrum
L 12-7 Infrared Spectroscopy of
Hydrocarbons
L 12-8 Characteristic
Absorptions of Alcohols and Amines
L 12-9 Characteristic
Absorptions of Carbonyl Compounds
L 12-10 Characteristic
Absorptions of C-N Bonds
L 12-11 Simplified Summary of IR
Stretching Frequencies
L 12-12 Reading and Interpreting
Infrared Spectra (Solved Problems)
L 12-13 Introduction to Mass
Spectrometry
L 12-14 Determination of the
Molecular Formula by Mass Spectrometry
L 12-15 Fragmentation Patterns
in Mass Spectrometry
13. Nuclear Magnetic Resonance Spectroscopy
L 13-2 Theory of Nuclear
Magnetic Resonance
L 13-3 Magnetic Shielding by
Electrons
L 13-4 The NMR Spectrometer
L 13-5 The Chemical Shift
L 13-6 The Number of Signals
L 13-7 Areas of the Peaks
L 13-8 Spin-Spin Splitting
L 13-9 Low-Field and High-Field
NMR Spectra
L 13-10 Complex Splitting
L 13-11 Stereochemical
Nonequivalence of Protons
L 13-12 Time Dependence of NMR
Spectroscopy
L 13-13 Carbon-13 NMR
Spectroscopy
L 13-14 Interpreting of Carbon
NMR Spectra
L 13-15 Nuclear Magnetic
Resonance Imaging
10. Structure and Synthesis
of Alcohols
10-2 Structure and Classification of Alcohols
10-3 Nomenclature of Alcohols and Phenols
10-4 Physical Properties of Alcohols
10-5 Commercially Important Alcohols
10-6 Acidity of Alcohols and Phenols
10-7 Synthesis of Alcohols: Introduction and Review
10-8 Organometallic Reagents for Alcohol Synthesis
10-9 Addition of Organometallic Reagents to Carbonyl Compounds
10-10 Side Reactions of Organometallic Reagents; Reduction of Alkyl
Halides
10-11 Reduction of the Carbonyl Group: Synthesis of 1o
and 2o Alcohols
O 10-12
Thiols (Mercaptans)
11. Reactions of Alcohols
11-1 Oxidation States of Alcohols and Related Functional Groups
11-2 Oxidation of Alcohols
11-3 Additional Methods for Oxidizing Alcohols
O 11-4 Biological
Oxidation of Alcohols
11-5 Alcohols as Nucleophiles and Electrophiles; Formation of
Tosylates
11-6 Reduction of Alcohols
11-7 Reactions of Alcohols with Hydrohalic Acids
11-8 Reactions of Alcohols with Phosphorus Halides
11-9 Reactions of Alcohols with Thionyl Chloride
11-10 Dehydration Reactions of Alcohols
11-11 Unique Reactions of Diols
11-13 Esters of Inorganic Acids
11-14 Formation and Reactions of Alkoxides
14. Ethers, Epoxides, and
Sulfides
14-2 Physical Properties of Ethers
14-3 Nomenclature of Ethers
14-3 Nomenclature of Ethers
14-4 Spectroscopy of Ethers
14-5 The Williamson Ether Synthesis
14-6 Synthesis of Ethers by
Alkoxymercuration-Demercuration
14-7 Synthesis of Ethers by Bimolecular
Dehydration of Alcohols (industrial Method)
14-8 Cleavage of Ethers by HBr and HI
14-9 Autoxidation of Ethers
O 14-10 Sulfides (Thioethers)
14-11 Synthesis of Epoxides
14-12 Acid-Catalyzed Ring Opening of Epoxides
14-13 Base-Catalyzed Ring Opening of Epoxides
14-14 Orientation of Epoxide Ring Opening
14-15 Reactions of Epoxides with Grignard and
Organolithium Reagents
X 14-16 Epoxy Resins: The Advent
of Modem Glues
18. Ketones and Aldehydes
18-1 Carbonyl Compounds
18-2 Structure of the Carbonyl Group
18-3 Nomenclature of Ketones and Aldehydes
18-4 Physical Properties of Ketones and
Aldehydes
18-5 Spectroscopy of Ketones and Aldehydes
18-6 Industrial Importance of Ketones and
Aldehydes
18-7 Review of Syntheses of Ketones and
Aldehydes
18-8 Synthesis of Ketones and Aldehydes Using
1,3-Dithianes
18-9 Synthesis of Ketones from Carboxylic Acids
18-10 Synthesis of Ketones from Nitriles
18-11 Synthesis of Aldehydes from Acid Chlorides
18-12 Reactions of Ketones and Aldehydes:
Nucleophilic Addition
18-13 Nucleophilic Addition of Phosphorus
Halides: The Wittig Reaction
18-14 Nucleophilic Addition of Water: Hydration
of Ketones and Aldehydes
19. Amines
19-2 Nomenclature of Amines
19-3 Structure of Amines
19-4 Physical Properties of Amines
19-5 Basicity of Amines
19-6 Effects on Amine Basicity
19-7 Salts of Amines
19-8 Amine Salts as Phase-Transfer Catalysts
19-9 Spectroscopy of Amines
19-10 Reactions of Amines with Ketones and Aldehydes
19-11 Aromatic Substitution of Aryl and Heterocyclic Amines
19-12 Alkylation of Amines by Alkyl Halides
19-13 Acylation of Amines by Acid Chlorides
19-14 Reaction of Amines with Sulfonyl Chlorides: Sulfonamides
19-15 Amines as Leaving Groups: The Hofmann Elimination
19-16 Oxidation of Amines: the Cope Elimination
19-17 Reactions of Amines with Nitrous Acid
19-18 Reactions of Arenediazonium Salts
19-19 Synthesis of Amines by Reductive Amination
19-20 Synthesis of Amines by Acylation-Reduction
19-21 Reduction of Nitro Compounds: Synthesis
of Arylamines
19-22 Direct Alkylation of Ammonia and Amines
19-23 Reduction of Azides and Nitriles to
Primary Amines
19-24 The Gabriel Synthesis of Primary Amines
19-25 The Hofmann Rearrangement of Amides
20. Carboxylic Acids
20-4 Acidity of Carboxylic Acids
20-5 Salts of Carboxylic Acids
20-6 Commercial Sources of Carboxylic Acids
20-7 Spectroscopy of Carboxylic Acids
20-8 Synthesis of Carboxylic Acids
20-9 Reactions of Carboxylic Acids and Their
Derivatives; Nucleophilic Acyl Substitution
20-10 Condensation of Acids with Alcohols: The
Fischer Esterification
20-11 Synthesis and Use of Acid Chlorides
20-12 Esterification Using Diazomethane
20-13 Condensation of Acids with Amines: Direct
Synthesis of Amides
20-14 Reduction of Carboxylic Acids
20-15 Alkylation of Carboxylic Acids to Form
Ketones
21. Carboxylic Acid Derivatives
21-2 Structure and Nomenclature of Acid
Derivatives
21-3 Physical Properties of Carboxylic Acid
Derivatives
21-4 Spectroscopy of Carboxylic Acid
Derivatives
21-5 Interconversion of Acid Derivatives by Nucleophilic
Acyl Substitution
21-6 Acid-Catalyzed Nucleophilic Acyl
Substitution
21-7 Hydrolysis of Carboxylic Acid Derivatives
21-8 Reduction of Acid Derivatives
21-9 Reactions of Acid Derivatives with
Organometallic Reagents
21-15 Thioesters
21-16 Esters and Amides of Carbonic Acid
22. Alpha Substitutions and Condensations of
Enols and Enolate Ions
22-2 Enols and Enolate Ions
22-3 a-Halogenation of Ketones
22-4 a-Bromination of Acids: the HVZ Reaction
22-5 Alkylation of Enolate Ions
22-6 Formation and Alkylation of Enamines
22-7 The Aldol Condensation of Ketones and
Aldehydes
22-8 Dehydration of Aldol Products
22-9 Crossed Aldol Condensations
22-10 Aldol Cyclizations
22-11 Planning Syntheses Using Aldol
Condensations
22-12 The Claisen Ester Condensation
22-13 The Dieckmann Condensation: A Claisen
Cyclization
22-14 Crossed Claisen Condensations
22-15 Syntheses Using b-Dicarbonyl Compounds
22-16 The
Malonic Ester Synthesis
22-17 The Acetoacetic Ester Synthesis
22-18 Conjugate Additions: The Michael Reaction
22-19 The Robinson Annulation
23. Carbohydrates and Nucleic Acids
B 23-2 Classification of
Carbohydrates
B 23-3 Monosaccharides
B 23-4 Erythro and Threo
Diastereomers
B 23-5 Epimers
B 23-6 Cyclic Structures of
Monosaccharides
B 23-7 Anomers of
Monosaccharides; Mutarotation
B 23-8 Reactions of
Monosaccharides: Side Reactions in Base
B 23-9 Reduction of Monosaccharides
B 23-10 Oxidation of
Monosaccharides; Reducing Sugars
B 23-11 Nonreducing Sugars:
Formation of Glycosides
B 23-12 Ether and Ester
Formation
B 23-13 Reactions with
Phenylhydrazine: Osazone Formation
B 23-14 Chain Shortening: The Ruff Degradation
B 23-15 Chain Lengthening: The
Kiliani-Fischer Synthesis
B 23-16 Fischer's Proof of the
Configuration of Glucose
B 23-17 Determination of Ring
Size; Periodic Acid Cleavage of Sugars
B 23-18 Disaccharides
B 23-19 Polysaccharides
B 23-20 Nucleic Acids:
Introduction
B 23-21 Ribonucleosides and
Ribonucleotides
B 23-22 The Structure of
Ribonucleic Acid
B 23-23 Deoxyribose and the
Structure of Deoxyribonucleic Acid
24. Amino Acids, Peptides, and Proteins
B 24-2 Structure and
Stereochemistry of the "-Amino Acids
B 24-3 Acid-Base Properties of
Amino Acids
B 24-4 Isoelectric Points and
Electrophoresis
B 24-5 Synthesis of Amino
Acids
B 24-6 Resolution of Amino
Acids
B 24-7 Reactions of Amino
Acids
B 24-8 Structure and
Nomenclature of Peptides and Proteins
B 24-9 Peptide Structure
Determination
B 24-10 Solution-Phase Peptide
Synthesis
B 24-11 Solid-Phase Peptide
Synthesis
B 24-12 Classification of
Proteins
B 24-13 Levels of Protein
Structure
B 24-14 Protein Denaturation
25. Lipids
B 25-2 Waxes
B 25-3 Triglycerides
B 25-4 Saponification of Fats
and Oils; Soaps and Detergents
B 25-5 Phospholipids
B 25-6 Steroids
B 25-7 Prostaglandins
B 25-8 Terpenes
26. Synthetic Polymers
B 26-2 Addition Polymers
B 26-3 Stereochemistry of
Polymers
B 26-4 Stereochemical Control
of Polymerization: Ziegler-Natta Catalysts
B 26-5 Natural and Synthetic
Rubbers
B 26-6 Copolymers of Two or
More Monomers
B