John McMurry: Organic Chemistry, 2004. Thomson/Brooks/Cole. ISBN: 0-534-42005-2. Utgave 6. http://www.brookscole.com/chemistry_d/index.html
F?lgende delavsnitt inng?r i pensum:
Kap. 1 Structure and Bonding
- 1.1. Atomic structure
- 1.2. Atomic structure: Orbitals
- 1.3. Atomic structure: Eletron configuration
- 1.4. Development of chemical bonding theory
- 1.5. The nature of chemical bonds
- 1.6. Valence bond theory
- 1.7. Hybridization: sp3 Orbitals and the structure of methane
- 1.8. Hybridization: sp3 Orbitals and the structure of ethane
- 1.9. Hybridization: sp2 Orbitals and the structure of ethylene
- 1.10. Hybridization: sp Orbitals and the structure of acetylene
- 1.11. Hybridization of nitrogen and oxygen
- 1.12. Molecular orbital theory
Kap. 2 Polar Covalent Bonds, Acids and Bases
- 2.1. Polar bovalent bonds: Eletronegativity
- 2.2. Polar covalent bonds: Dipole moments
- 2.3. Formal charges
- 2.4. Resonance
- 2.5. Rules for resonance rorms
- 2.6. Drawing resonance forms
- 2.7. Acids and bases: The Br?nsted-Lowry definition
- 2.8. Acid and base strength
- 2.9. Prediciting acid-base reactions from pKa values
- 2.10. Organic acids and bases
- 2.11. Acids and bases: The Lewis definition
- 2.12. Drawing chemical structures
- 2.13. Molecular models
Kap. 3 Organic Compounds: Alkanes and Cycloalkanes
- 3.1. Functional groups
- 3.2. Alkanes and alkane isomers
- 3.3. Alkyl groups
- 3.4. Naming alkanes
- 3.5. Properties of alkanes
- 3.6. Cycloalkanes
- 3.7. Naming cycloalkanes
- 3.8. Cis-trans isomerism in cycloalkanes
Kap. 4 Stereochemistry of Alkanes and Cycloalkanes
- 4.1. Conformation of ethane
- 4.2. Conformation of propane
- 4.3. Conformation of butane
- 4.4. Stability of cycloalkanes: The Baeyer strain theory
- 4.5. The nature of ring strain
- 4.6. Cyclopropane: An orbital view
- 4.7. Conformations of cyclobutane and cyclopentane
- 4.8. Conformations of cyclohexane
- 4.9. Axial and equatorial bonds in cyclohexane
- 4.10. Conformational mobility of cyclohexane
- 4.11. Conformations of monosubstituted cyclohexanes
- 4.12. Conformational analysis of disubstituted cyclohexanes
- 4.13. Boat cyclohexane
- 4.14. Conformations of polycyclic molecules
Kap. 5 An Overview of Organic Reactions
- 5.1. Kinds of organic reactions
- 5.2. How organic reactions occur: Mechanisms
- 5.3. Radical reactions and how they occur
- 5.4. Polar reactions and how they occur
- 5.5. An example of a polar reaction addition of HBr to ethylene
- 5.6. Using curved arrows in polar reaction mechanisms
- 5.7. Describing a reaction: Equilibria, rates, and energy
- 5.8. Describing a reaction: Bond dissociation energies
- 5.9. Describing a reaction: Energy diagrams and transition states
- 5.10. Describing a reaction: Intermediates
Kap. 6 Alkenes: Structure and Reactivity
- 6.3. Naming alkenes
- 6.4. Electronic structure of alkenes
- 6.5. Cis-trans isomerism in alkenes
- 6.6. Sequence rules: The E,Z designation
- 6.7. Alkene stability
- 6.8. Electrophilic addition of HX to alkenes
- 6.9. Orientation of electrophilic addition: Markovnikov’s Rule
- 6.10. Carbocation structure and stability
Kap. 7 Alkenes: Reactions and Synthesis
- 7.1. Preparation of alkenes: A preview of elimination reactions
- 7.2. Addition of halogens to alkenes
- 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. 9 Stereochemistry
- 9.1. Enantiomers and the tetrahedral carbon
- 9.2. The reason for handedness in molecules: Chirality
- 9.3. Optical activity
- 9.4. Pasteur's discovery of enantiomers
- 9.5. Sequence rules for specification of configuration
- 9.6. Diastereomers
- 9.7. Meso compounds
- 9.8. Molecules with more than two chirality centers
- 9.9. Physical properties of stereoisomers
- 9.10. Racemic mixtures and their resolution
- 9.11. A brief review of isomerism
- 9.12. Stereochemistry of reactions: Addition of HBr to alkenes
- 9.13. Stereochemistry of reactions: Addition of Br2 to alkenes
- 9.14. Stereochemistry of reactions: Addition of HBr to chiral alkenes
- 9.15. Chirality at atoms other than carbons
- 9.16. Chirality in nature
- 9.17. Prochirality
Kap. 10 Alkyl Halides
- 10.1. Naming alkyl halides
- 10.2. Structure of alkyl halides
- 10.3. Preparation of 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 alkyl halides: Grignard reagents
- 10.10. Oxidation and reduction in organic chemistry
Kap. 11 Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
- 11.1. The discovery of the Walden inversion
- 11.2. Stereochemistry of nucleophilic substitution
- 11.3. Kinetics of nucleophilic substitution
- 11.4. The SN2 reaction
- 11.5. Characterisation of the SN2 reaction
- 11.6. The SN1 reaction
- 11.7. Kinetics of the SN1 reaction
- 11.8. Stereochemistry of the SN1 reaction
- 11.9. Characteristics of the SN1 reaction
- 11.10. Elimination reactions of alkyl halides: Zaitsev’s rule
- 11.11. The E2 reaction
- 11.12. Elimination reactions and cyclohexane conformation
- 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. Electrophilic additions to conjugated dienes; allylic carbocations
- 14.4. Kinetic versus thermodynamic control of reactions
- 14.5. The Diels Alder cycloaddition reaction
- 14.6. Characteristics of the Diels Alder reaction
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. 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”