Contents Preface 1 Structure and bonding 1 nc versus covalent bonds The octet rule Formal charge Sigma(-)and pi(-)bonds Hybridisation 22346 1.6 Inductive effects,hyperconjugation and mesomeric effects 1.6.1 Inductive effects Hyperconjugation 1.6.3 Mesomeric effects 1.7 Acidity and basicity 6779 1.7.1 Acids 1.72 Bases 1.7.3 Lewis acids and bases 912155 1.7.4 Basicity and hybridisation 1.7.5 Acidity and aromaticity 6 1.7.6 Acid-base reactions Worked example 17 Problems 1 2 Functional nomenclature and drawing organic compo groups 23 Alkyl an aryl groups 2.4 Alkyl subs 241 2.5 Drawing organic structures 112335289 rked example Problems 3.1 Isomerism 31 3.2 Confo 3.21 onal isomers of ethane(CH,CH3) 32 3.2.2 of e(CH,CH2CH2CH3) 3 3.2.3 Conformations of eycloalkanes 34Contents Preface xi 1 Structure and bonding 1 1.1 Ionic versus covalent bonds 1 1.2 The octet rule 2 1.3 Formal charge 2 1.4 Sigma (s
) and pi (p
) bonds 3 1.5 Hybridisation 4 1.6 Inductive effects, hyperconjugation and mesomeric effects 6 1.6.1 Inductive effects 6 1.6.2 Hyperconjugation 7 1.6.3 Mesomeric effects 7 1.7 Acidity and basicity 9 1.7.1 Acids 9 1.7.2 Bases 12 1.7.3 Lewis acids and bases 15 1.7.4 Basicity and hybridisation 15 1.7.5 Acidity and aromaticity 16 1.7.6 Acid-base reactions 16 Worked example 17 Problems 18 2 Functional groups, nomenclature and drawing organic compounds 21 2.1 Functional groups 21 2.2 Alkyl and aryl groups 22 2.3 Alkyl substitution 23 2.4 Naming carbon chains 23 2.4.1 Special cases 25 2.5 Drawing organic structures 27 Worked example 28 Problems 29 3 Stereochemistry 31 3.1 Isomerism 31 3.2 Conformational isomers 32 3.2.1 Conformations of ethane (CH3CH3) 32 3.2.2 Conformations of butane (CH3CH2CH2CH3) 33 3.2.3 Conformations of cycloalkanes 34