Organic chemistry 2004/9/28, based on lecture files
The following parts or sections in the textbook are what you can skipped
以下章節部分，可以不讀，考試也不會考。
有些章節甚大如有分A, B, C, D…等部分若未特別寫出，則指整個章節。但若有指明(如15-11B)， 則該節其他部分(如15-11A, 15-11C, 15-11D…)還是要讀
Chapter 9: alkynes 9-4 and 9-6B
Chapter 10: Structure and synthesis of alcohols: 10-9D and 10-10B
Chapter 11: Reactions of alcohols: 11-4, 11-5, 11-8, 11-9, 11-13, 11-14, (pinacol rearrangement)
Chapter 12 IR and Mass: 12-6, 12-7, 12-8, 12-9, 12-10, 12-11, 12-12, 12-15,
Chapter 13 NMR: 13-5B, 13-8C, 13-8D, 13-9, 13-10, 13-11, 13-12, 13-13, 13-14
Chapter 14 Ethers: 14-4, 14-10
Chapter 15 Conjugated systems: 15-8, 15-9, 15-10, 15-11B, 15-12,
Chapter 16 Aromatic compounds:16-4, 16-7, 16-10, 16-11, 16-12, 16-14, 16-15,
Chapter 17 Reactions of aromatics: 17-11C, 17-15
Practice the following questions:
Sample problems in the text and the following
Chapter 9: 9-33
Chapter 10: 10-35, 10-36, 10-38
Chapter 11: 11-43, 11-44
Chapter 12: 12-12,
Chapter 13: 13-3, 13-4, 13-33, 13-34,
Chapter 14: 14-1, 14-14, solved 14-2, 14-29
Chpater 15: 15-1, 15-11, 15-16, solved 15-3,
Chapter 16: 16-8, 16-15, 16-22, 16-32
Chapter 17: 17-14, 17-30, 17-48,
Examination: key points
Chapter 9: acidity, reactions (addition of water, alcohols, HX, H2-cis-trans)
Chapter 10: basic properties, Grignard reagent and its reactions to generate alcohols, LiAlH4/NaBH4, diols,
Chapter 11: substitution reactions, dehydration, cleavage, periodate oxidation, esterification
Chapter 12: basic knowledges of IR and mass, isotope effect on mass spectrum
Chapter 13: equivalent hydrogens, NMR spectrum, chemical shift, signal splitting, structural analysis,
Chapter 14: basic properties, Williamson synthesis, cleavage, oxidation, epoxide ring opening acidic-basic conditions), glue
Chapter 15: properties of conjugated system (heat of hydrogenation, 财max), the natural diene unit, allylic halogenation, thermodynamic/kinetic control products, D-A reaction,
Chapter 16: criteria of aromaticity, Huckle’s rule, aromaticity or anti or non-, cyclo-propenyl, cyclopentadienyl, tropylium, azulene, heterocyclic aromatics, nomenclature of some aromatic compounds.
Chapter 17: EAS, attacking electrophilies, reagents used, products formed, the site-preference and reactivity in disubstitution, Birch reduction, benzylic reactions,
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