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Chapter 11. Infrared Spectroscopy and Mass Spectrometry

1.The Electromagnetic Spectrum, Visible Light and Color

2.Infrared Spectroscopy

2.1Wavelength and Wavenumbers

3.Molecular Vibrations

4.Characteristic Absorptions

5.Simplified Summary of IR Stretching Frequencies

5.1Solving IR Problems

6.Introduction to Mass Spectrometry

7.Determination of the Molecular Formula by Mass Spectrometry

7.1Molecular Ions

7.2Isotopes

7.3Nitrogen Rule

8. Fragmentation Patterns in Mass Spectrometry

9. Solving MS problems

10. Solving Problems with IR and MS

Chapter 12. Nuclear Magnetic Resonance

1. Theory of Nuclear Magnetic Resonance

1.1 Nuclear Spin

2. Magnetic Shielding by Electrons

3. The NMR Spectrometer

4. The Chemical Shift

5. The Number of Signals

6. Areas of Peaks

7. Spin-Spin Coupling

7.1 Complex Splitting

7.2 Stereochemical Non-equivalence of protons

8. Solving NMR spectra

8.1 Practice Problems

9. Carbon-13 NMR

9.1 Interpreting C-13 NMR

10. Integrated Structure Determination

10.1 IR and NMR

10.2 IR, MS and NMR

Chapter 13. Conjugation

1. Stabilities of Dienes

2. Molecular Orbital Picture of a Conjugated System

3. Allylic Cations

4. 1,2- and 1,4-Addition to Conjugated Dienes

4.1 Kinetic versus Thermodynamic control in the Addition of HBr to Buta-1,3-diene

5. Allylic Radicals

6. Molecular Orbitals of the Allylic System

6.1 Electronic configurations of the Allyl Radical, Cation, and Anion

7. SN2 Displacement Reactions of Allylic Halides and Tosylates

8. The Diels-Alder Reaction

8.1 The Diels-Alder as an Example of a Pericyclic Reaction

9. Ultraviolet Absorption Spectroscopy

9.1 Colored Organic compounds

Chapter 14. Aromaticity

1. The Discovery of Benzene

2. The Structure and Properties of Benzene

2.1 Stability of Benzene

3. Aromaticity

3.1 Huckel’s Rule

4. The Molecular Orbitals of Benzene

4.1 Frost Diagrams

5. Aromatic, Antiaromatic, and Nonaromatic Compounds

6. Examples of Aromatic Molecules

6.1 Aromatic Ions

6.2 Heterocyclic Aromatic Compounds

6.3 Polynuclear Aromatic Hydrocarbons

6.4 Aromatic Allotropes of Carbon

6.5 Fused Heterocyclic Compounds

7. Nomenclature of Benzene Derivatives

Chapter 15. Reactions of Aromatic Compounds

1. Electrophilic Aromatic Substitution

1.1 Halogenation of Benzene

1.2 Nitration of Benzene

1.3 Sulfonation of Benzene

2. Friedel-Crafts Reactions

2.1 Alkylation

2.2 Acylation

3. Di- and Polysubstitution: Substitution effects on orientation

3.1 Theory of Directing effects

3.2 Activating, Ortho, Para-Directing Substituents

3.3 Deactiving, Meta-Directors

3.4 Halogen Substituents: Deactivating, but Ortho- Para-Directing

4. Nucleophilic Aromatic Substitution

4.1 Benzyne Intermediates

5. Birch Reduction of Aromatic Molecules

5.1 Regioselectivity of Birch Reduction

6. Side-Chain Reactions of Benzene Derivatives

6.1 Oxidation

6.2 Free Radical Halogenation

6.3 Substitution (S_N1 and S_N2)

6.4 Hydrogenolysis

7. Summary of Phenols

7.1 Acidity

7.2 Oxidation

7.3 Electrophilic Aromatic Substitution

Chapter 16: Ketones and Aldehydes

1. Carbonyl compounds

2. Structure of the Carbonyl Group

3. Nomenclature of Ketones and Aldehydes

4. Physical Properties of Ketones and Aldehydes

Review: Synthesis of Ketones and Aldehydes

5. Reactions of Ketones and Aldehydes: Introduction to Nucleophilic addition

6. Reactions of Ketones and Aldehydes: Addition of Carbon Nucleophiles

6.1 Grignard, Organolithium and other Organometallic Reagents

6.2 Cyanide: Formation of Cyanohydrins

6.3 Deprotonated Alkynes

7. The Wittig Reaction

8. Hydration of Ketones and Aldehydes

9. Formation of acetals

9.1 Use of acetals as protecting groups

10. Reactions with amines

10.1 Formation of imines

10.2 Condensations with Hydroxylamine and hydrazines

11. Oxidation of Aldehydes

12. Reductions of Ketones and Aldehydes

12.1 Metal Hydride

12.2 Other reductions

Chapter 17: Carboxylic Acids

1......... Nomenclature of Carboxylic Acids

2......... Structure and Physical Properties of Carboxylic Acids

3......... Acidity of Carboxylic Acids

........... 3.1 Origins of Acidity of Carboxylic Acids

........... 3.2 Salts of Carboxylic Acids

........... 3.3 Natural sources of Carboxylic Acids

4. ...... Synthesis of Carboxylic Acids

5. ...... Condensation of Acids with Alcohols: the Fischer Esterification

........... 5.1 Esterification Using Diazomethane

6. ...... Reduction of Carboxylic Acids

........... 6.1 Alkylation of Carboxylic Acids to Form Ketones

7. ...... Synthesis of Acid Chlorides

Chapter 18: Carboxylic Acid Derivatives

1. Structure and Nomenclature of Acid Derivatives

2. Physical Properties of Carboxylic Acid Derivatives

3. Substitution of Carboxylic Acid Derivatives by Nucleophilic Acyl Substitution

3.1 Substitutions of Acid Chloride

3.2 Substitutions of Acid Anhydrides

3.3 Substitutions of Esters

3.3.1 Transesterification

3.4 Amides

4. Hydrolysis of Carboxylic Acid Derivatives

5. Reduction of Acid Derivatives

6. Reactions of Acid Derivatives with Organometallic Reagents

Chapter 19: Carbonyl Condensation Reactions

Enols and Enolate Ions
1. 1 Acidity of alpha-Hydrogens
Alpha-Halogenation
Alkylation of Enolates
The Aldol Condensation of Ketones and Aldehydes
1. 1 Base Catalyzed
2. 2 Acid Catalyzed
3. 3 Dehydration of Aldol Products
4. 4 Crossed Aldol Condensations
5. 5 Aldol Cyclizations
Planning Syntheses Using Aldol Condensations
Enamines
The Claisen Ester Condensation
1. 1 The Dieckmann Condensation: A Claisen Cyclization
2. 2 Crossed Claisen Condensations

Chapter 20: Amines

Nomenclature of Amines
Structure and Physical Properties of Amines
1. 1 Chirality
Basicity of Amines
1. 1 Salts of Amines
2. 2 Natural Products
Review: Reactions of Amines with Ketones and Aldehydes
Other Reactions of Amines
1. 1 Alkylation of Amines by Alkyl Halides
2. 2 The Hofmann Elimination
3. 3 Acylation of Amines by Acid Chlorides
4. 4 Oxidation of Amines; The Cope Elimination
Synthesis and Reactions of Arenediazonium Salts
Synthesis of Amines
1. 1 Reductive Amination
2. 2 Synthesis of Amines by Acylation-Reduction
3. 3 Syntheses Limited to Primary Amines

Chapter 21. Carbon-Carbon Bond Formation and Chiral Catalysis

1. Palladium-catalyzed Cross-Coupling Reactions

1 Heck Reaction
2 Suzuki Coupling
3 Other Reactions
1. Stille Coupling
2. Sonagashira Coupling
3. Negishi Coupling

2. Alkene Metathesis

Grubbs Catalyst

Synthesis of Single Enantiomers
1. 1 Asymmetric Induction
  1. Chiral Auxiliary
2. 2 Chiral Catalysis

Chapter 22. Carbohydrates

Classification of Carbohydrates
1. Fisher Projections

Monosaccharides
D and L Sugars
Epimers
Cyclic Structures of Monosaccharides
1. Haworth Projections
Anomers of Monosaccharides
Glycosidic bonds
Disaccharides
1. 1 Sucrose vs HFCS
Polysaccharides