International Chemistry Olympiad - Appendix C ... - PianetaChimica

. Strain in small rings 3c. chair/boat conformations of cyclohexane 39.2.2. Alkenes9.2.2.1. Products from Br 2 , HBr and H 2 O/H + 19.2.2.2. Markownikoff’s rule 29.2.2.3. Mechanism involving carbocation intermediates 39.2.2.4. Relative stability of carbocations 39.2.2.5. 1,4 addition to dienes 39.2.3. Alkynes9.2.3.1. Acidity relative to alkenes 39.2.3.2. Differences in chemical properties from alkenes 29.2.4. Benzene9.2.4.1. formula 19.2.4.2. stabilization by resonance 19.2.4.3. electrophilic substitution (nitration, halogenation)a. directing effect of first substituent 3b. effect of first substituent on reactivity 3c. explanation of substituent effects 39.2.5. Halogen compounds9.2.5.1. Nomenclature of monofunctional 19.2.5.2. Substitution reactionsa. giving alcohols 3b. in which halogen is exchanged 3c. reactivityi. primary vs secondary vs tertiary 3ii. aliphatic vs aromatic 3d. S N 1 and S N 2 mechanisms 39.2.5.3. Elimination reactions 29.2.5.4. Competition of elimination and substitution 29.2.6. Alcohols9.2.6.1. Nomenclature of monofunctional 19.2.6.2. Comparison of acidity of alcohols and phenols 29.2.6.3. Dehydration to alkenes 19.2.6.4. Esters with inorganic acid 29.2.6.5. Oxidation reactions 19.2.7. Aldehydes and ketones9.2.7.1. Nomenclature of monofunctional 19.2.7.2. Oxidation of aldehydes 19.2.7.3. Reduction to alcohols (LiAlH 4 , NaBH 4 ) 39.2.7.4. Keto/enol tautomerism 39.2.7.5. Nucleophilic addition reactions witha. HCN 3b. RNH 2 (R = alkyl, HO, NH 2 ) 3c. enolate anions (aldol condensation) 3d. alcohols to form acetals/ketals 3e. Grignard reagents 39.2.8. Carboxylic acids and their derivatives9.2.8.1. Nomenclature of carboxylic acids and their derivatives(esters, acid halides, amides)9.2.8.2. Acidity strength related to inductive effects 39.2.8.3. Preparation of carboxylic acids by hydrolysis ofa. esters (including soaps) 1b. amides 2c. nitriles 3International Chemistry Olympiad - Appendix C - 2004 72