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              26-7     Condensation Polymers

B              26-8     Polymer Structure and Properties