1.1 atoms and molecules; 1.2 heats of formation and reaction; 1.3 bonding models; 1.4 complementary descriptions of the double bond; 1.5 choosing models in organic chemistry; chapter 2: stereochemistry; 2.1 introduction; 2.2 stereoisomerism; 2.3 manifestations of stereoisomerism; 2.4 stereotopicity; chapter 3: conformational analysis and molecular mechanics; 3.1 molecular conformation; 3.2 conformational analysis; 3.3 molecular mechanics. 3.4 molecular strain and limits to molecular stabilitychapter 4: applications of molecular orbital theory and valence bond theory; 4.1 introduction to molecular orbital theory; 4.2 aromaticity; 4.3 contemporary computational methods; 4.4 valence bond theory; chapter 5: reactive intermediates; 5.1 reaction coordinate diagrams; 5.2 radicals; 5.3 carbenes; 5.4 carbocations; 5.5 carbanions; 5.6 choosing models of reactive intermediates; chapter 6: methods of studying organic reactions; 6.1 molecular change and reaction mechanisms; 6.2 methods to determine reaction mechanisms. 6.3 applications of kinetics in studying reaction mechanisms6.4 arrhenius theory and transition-state theory; 6.5 reaction barriers and potential energy surfaces; 6.6 kinetic isotope effects; 6.7 substituent effects; 6.8 linear free energy relationships; chapter 7: acid and base catalysis of organic reactions; 7.1 acidity and basicity of organic compounds; 7.2 acid and base catalysis of chemical reactions; 7.3 acid and base catalysis of reactions of carbonyl compounds and carboxylic acid derivatives; chapter 8: substitution reactions; 8.1 introduction; 8.2 nucleophilic aliphatic substitution. 8.3 electrophilic aromatic substitution8.4 nucleophilic aromatic and vinylic substitution; chapter 9: addition reactions; 9.1 introduction; 9.2 addition of halogens to alkenes; 9.3 other addition reactions; chapter 10: elimination reactions; 10.1 introduction; 10.2 dehydrohalogenation and related 1,2-elimination reactions; 10.3 other 1,2-elimination reactions; chapter 11: pericyclic reactions; 11.1 introduction; 11.2 electrocyclic transformations; 11.3 sigmatropic reactions; 11.4 cycloaddition reactions; 11.5 other concerted reactions; 11.6 a general selection rule for pericyclic reactions. 11.7 alternative conceptual models for concerted reactionschapter 12: photochemistry; 12.1 photophysical processes; 12.2 fundamentals of photochemical kinetics; 12.3 physical properties of excited states; 12.4 representative photochemical reactions; 12.5 some applications of organic photochemistry