John McMurry: Organic Chemistry, 2004. Thomson/Brooks/Cole. ISBN: 0-534-38999-6. Utgave 6 (utgave 5 kan benyttes). http://www.brookscole.com/chemistry_d/index.html.
Følgende delavsnitt inngår i pensum (avsnittnummer i parentes er til utgave 5 der det er forskjeller):
- Kap. 6 Alkenes: Structure and Reactivity
- 6.9. Orientation of electrophilic addition
- Kap. 7 Alkenes: Reactions and Synthesis
- 7.1. Preparation of alkenes: A preview of elimination reactions
- 7.2. Addition of halogens to alkenes
- 7.3. Halohydrin formation
- 7.4. Addition of water to alkenes: Oxymercuration
- 7.5. Addition of water to alkenes: Hydroboration
- 7.7. Reduction of alkenes: Hydrogenation
- 7.8. Oxidation of alkenes: Hydroxylation and cleavage
- Kap. 8 Alkynes: An Introduction to Organic Synthesis
- 8.1. Electronic structure of alkynes
- 8.2. Naming alkynes
- 8.3. Preparation of alkynes: Elimination reactions of dihalides
- 8.4. Reactions of alkynes: Addition of HX and X2
- 8.6. Reduction of alkynes
- 8.8. Alkyne acidity: Formation of acetylide anions
- 8.9. Alkylation of acetylide anions
- 8.10. An introduction to organic synthesis
- Kap. 10 Alkyl Halides
- 10.3. Preparing alkyl halides
- 10.4. Radical halogenation of alkanes
- 10.5. Allylic bromination of alkenes
- 10.6. Stability of the allyl radical: Resonance revisited
- 10.7. Preparing alkyl halides from alcohols
- 10.8. Reactions of organohalides: Grignard reagents
- 10.10. Oxidation and reduction in organic chemistry
- Kap. 11 Reactions of Alkyl Halides: Nucleophilic Substitutions and Elimination
- 11.10. Elimination reactions of alkyl halides: Zaitsev’s rule
- 11.11. The E2 reaction
- 11.14. The E1 reaction
- 11.15. Summary of reactivity SN1, SN2, E1, E2
- 11.16. Substitution reactions in synthesis
- Kap. 12 Struture Determination: Mass Spectrometry and Infrared Spectroscopy
- 12.1. Mass spectrometry
- 12.2. Interpreting mass spectra
- 12.3. Interpreting mass spectral fragmentation patterns
- 12.4. Mass spectral behavior of some common functional groups
- 12.5. Spectroscopy and the electromagnetic spectrum
- 12.6. Infrared spectroscopy of organic molecules
- 12.7. Interpreting infrared spectra
- 12.8. Infrared spectra of hydrocarbons
- 12.9. Infrared spectra of some common functional groups
- Kap. 13 Structure Determination: Nuclear Magnetic Resonace Spectroscopy
- 13.1. Nuclear magnetic resonance spectroscopy
- 13.2. The nature of NMR absorption
- 13.3. Chemical shifts
- 13.4. 13C NMR spectroscopy: Signal averaging and FT-NMR
- 13.5. Charactheristics of 13C NMR spectroscopy
- 13.8. 1H NMR spectroscopy and proton equivalence
- 13.9. Chemical shifts in 1H NMR spectroscopy
- 13.10. Integration of 1H NMR absorbtions: Proton counting
- 13.11. Spin-spin splitting in 1H NMR spectra
- Kap. 14 Conjugated Dienes and Ultraviolet Spectroscopy
- 14.1. Preparation of conjugated dienes
- 14.3 (14.5). Electrophilic additions to conjugated dienes: Allylic carbocations
- 14.4 (14.6). Kinetic versus thermodynamic control of reactions
- 14.5 (14.8). The Diels-Alder cycloaddition reaction
- 14.6 (14.9). Characteristics of the Diels Alder reaction
- Kap. 15 Benzene and Aromaticity
- 15.1. Sources of aromatic hydrocarbons
- 15.2. Naming aromatic compounds
- 15.3. Structure and stability of benzene
- 15.4. Molecular orbital description of benzene
- 15.5. Aromaticity and the Hückel 4n+2 rule
- 15.6. Aromatic ions
- 15.7. Aromatic heterocycles: Pyridine and pyrrole
- 15.8. Why 4n+2?
- 15.9. Polycyclic aromatic compound: Naphthalene
- 15.10. Spectroscopy of aromatic compounds
- Kap. 16 Chemistry of Benzene: Electrophilic Aromatic Substitution
- 16.1. Bromination of aromatic rings
- 16.2. Other aromatic substitutions
- 16.3. Alkylation of aromatic rings: The Friedel-Crafts reaction
- 16.4. Acylation of aromatic rings
- Kap. 17 Alcohols and Phenols
- 17.1. Naming alcohols and phenols
- 17.2. Properties of alcohols and phenols: Hydrogen bonding
- 17.3. Properties of alcohols and phenols: Acidity and basicity
- 17.4. Preparation of alcohols: A review
- 17.5. Alcohols from reduction of carbonyl compounds
- 17.6. Alcohols from reaction of carbonyl compounds with Grignard reagents.
- 17.7. Some reactions of alcohols
- 17.8. Oxidation of alcohols
- 17.12. Spectroscopy of alcohols and phenols
- Kap. 18 Ethers and Epoxides; Thiols and Sulfides
- 18.1. Naming ethers
- 18.2. Structure, properties, and sources of ethers
- 18.3. The Williamson ether synthesis
- 18.7. Cyclic ethers: Epoxides
- 18.8. Ring opening reactions of epoxides
- 18.10 (18.11). Thiols and sulfides
- 18.11 (18.10). Spectroscopy of ethers
- Kap. 19 Aldehydes and Ketones: Nucleophilic Addition Reactions
- 19.1. Naming aldehydes and ketones
- 19.2. Preparation of aldehydes and ketones
- 19.3. Oxidation of aldehydes and ketones
- 19.4. Nucleophilic addition reactions of aldehydes and ketones
- 19.5. Relative reactivity of aldehydes and ketones
- 19.6. Nucleophilic addition of H2O: Hydration
- 19.7. Nucleophilic addition of HCN: Cyanohydrin formation
- 19.8. Nucleophilic addition of Grignard reagents and hydride reagents: Alcohol formation
- 19.9. Nucleophilic addition of amines: Imine and enamine formation
- 19.11. Nucleophilic addition of alcohols: Acetal formation
- 19.12. Nucleophilic addition of phosphorus ylides: The Wittig reaction
- 19.16. Spectroscopy of aldehydes and ketones
- Kap. 20 Carboxylic Acids
- 20.1. Naming carboxylic acids and nitriles
- 20.2. Structure and physical properties of carboxylic acids
- 20.3. Dissociation of carboxylic acids
- 20.4. Substituent effects on acidity
- 20.5. Substituent effects in substituted benzoic acids
- 20.6. Preparation of carboxylic acids
- 20.7. Reactions of carboxylic acids: An overview
- 20.8. Reduction of carboxylic acids
- 20.9 (21.8). Chemistry of nitriles
- 20.10 (20.9). Spectroscopy of carboxylic acids and nitriles
- Kap. 21 Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions
- 21.1. Naming carboxylic acid derivatives
- 21.2. Nucleophilic acyl substitution reactions
- 21.3. Nucleophilic acyl substitution reactions of carboxylic acids
- 21.4. Chemistry of acid halides
- 21.5. Chemistry of acid anhydrides
- 21.6. Chemistry of esters
- 21.7. Chemistry of amides
- Kap. 22 Carbonyl Alpha-Substitution Reactions
- 22.1. Keto-enol tautomerism
- 22.2. Reactivity of enols: The mechanism of alpha-substitution 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
- Kap. 23 Carbonyl Condensation Reactions
- 23.1. Mechanism of carbonyl condensation
- 23.2. Condensation of aldehydes and ketones: The aldol reaction
- 23.3 Carbonyl Condensation Reactions versus Alpha-Substitution Reactions
- 23.4. Dehydration of aldol products: Synthesis of enones
- 23.5. Using aldol reactions in synthesis
- 23.6. Mixed aldol condensation
- 23.7. Intramolecular aldol condensation
- 23.8. The Claisen condensation reaction
- 23.9. Mixed Claisen condensation
- 23.10. Intramolecular Claisen condensations: The Dieckmann cyclization
- 23.11. The Michael reaction
- Kap. 24 Amines
- 24.1. Naming amines
- 24.2. Structure and bonding in amines
- 24.3. Properties and sources of amines
- 24.4. Basicity of amines
- 24.5. Basicity of substituted arylamines
- 24.6. Synthesis of amines; men bare avsnittet “Reduction of nitriles, amides, and nitro compounds”
- Kap. 25 Biomolecules: Carbohydrates
- 25.1. Classification of carbohydrates
- 25.2. Configurations of monosaccarides: Fisher projections
- 25.3. D,L sugars
- 25.4. Configuration of the aldoses
- 25.5. Cyclic structures of monosaccarides: Hemiacetal formation
- 25.6. Monosaccaride anomers: Mutarotation
- Kap. 26 Biomolecules: Amino Acids, Peptides and Proteins
- 26.1. Structures of amino acids
- 26.2. Isoelectric points