文稿大二有机下final

1、Final ReviewGive IUPAC names to the following compounds:2. Draw structures corresponding to the following IUPAC names:3. Predict the major product(s), or fill in the missing substrates in the following reactions:4. Short answer questions:5. Propose reasonable mechanisms to the following reactions:6.

2、 Synthesize the following target molecules from corresponding starting organic compounds and any inorganic compounds you need. 7. Structure determination (15%)Final ReviewChapter Ten Ethers and EpoxidesChapter Ten Ethers and Epoxides1. Chemical Properties of Ether(1). Oxonium Salts Formation of Ethe

3、rsApplication？(2). Acidic Cleavage of Ethers哪里断？2. Preparation of EthersChapter Ten Ethers and EpoxidesWilliamson Ether Synthesis混合醚的合成用相应的醇钠和卤代烃的亲核取代反应，用醇的分子间脱水的方法易得到混合物。醇的分子间脱水只适合用来合成简单的单醚。Chapter Ten Ethers and Epoxides3. Chemical Properties of EtherSN2SN1(1) Acid-Catalyzed Epoxides Opening(2) Ba

4、se-catalyzed Epoxides OpeningSN1?哪里开环？哪里开环？Chapter Ten Ethers and Epoxides4. Claisen Rearrangement Reactions of EthersRearrangement +Isomerization 合成增加两个碳原子的方法，关注有取代基的环氧乙烷此反应在哪里开环？Chapter Ten Ethers and Epoxides No Isomerization occurs5. Mechanism:Acid-CatalyzedEpoxides OpeningC+RearrangementElectro

5、phileChapter Eleven Aldehydes and KetonesFinal Review1. Nucleophilic Addition Reactions of Aldehydes and KetonesChapter Eleven Aldehydes and KetonesThe influencing factors of the reaction:(a) Electronic effect:+ Relative reactivity(b) Steric effectSteric hindrance Relative reactivity重要的中间体，多一个碳原子部分醛

6、酮的分离提纯，现象？2，4-二硝基苯肼的反应，用于醛酮的鉴定，制备烯烃的好方法反应的可逆性，可在反应中对羰基进行保护Witting 反应醛、甲基脂肪酮、C8以下环酮格式试剂和醛酮，生成各种结构的醇制备醇的好方法，注意反应有加成和酸性水解两步，写完整条件通常用二元醇，乙二醇pH = 4-5 ?可以转换成COOH, CH2NH2,条件？RLi, Organozinc Reagent? Chapter Eleven Aldehydes and Ketones2. Reactions of -H(a) The Aldol Reactions (羟醛缩合反应)The carbon chain incre

7、ase doubled.A good method to prepare ,-unsaturated aldehydes.(1)-H; (2) base COOHCH2OH产物通过选择性的氧化还原，可得多种化合物，关注！Chapter Eleven Aldehydes and KetonesMixed Aldol ReactionClaisen-Schmidt condensationsKnoevenagel condensationsPerkin Condensation(2) Alpha Halogenation(卤代) of Aldehydes and KetonesIntramolec

8、ular Aldol ReactionsCyclic compoundsApplication?3. Oxidation of Aldehydes and KetonesChapter Eleven Aldehydes and Ketones4. Reductions of Aldehydes and KetonesChapter Eleven Aldehydes and Ketones关注不同还原剂的选择性Chapter Eleven Aldehydes and KetonesThe Cannizzaro Reaction5. Preparation of Aldehydes and Ket

9、onesChapter Eleven Aldehydes and Ketones(1). Oxidative Cleavage of Alkenes. (2). Hydration of Alkynes (3). Oxidation of alcohols(4). Friedel-Crafts Acylation and Gattermann-koch reaction(5). Partially Reduction of Certain Carboxylic Acid Derivatives6. Conjugated Nucleophilic Addition to ,-Unsaturate

10、d Aldehydes and KetonesChapter Eleven Aldehydes and Ketones1, 2-additonStrongly basic nucleophiles: RMgX or RLi 1, 4-additonWeakly basic nucleophiles: RNH2 , HCNChapter Eleven Aldehydes and KetonesChapter Eleven Aldehydes and KetonesThe mechanism of acid-catalyzed reaction of an aldehyde or ketone w

11、ith an alcohol.7. Mechanism: (2) The mechanism of aldol reaction(3) The mechanism of Cannizzaro ReactionIR:1850-1700 cm-1Stretch：1H NMR: = 910 ppm= 22.5 ppmChapter Eleven Aldehydes and Ketones8. Spectroscopy of Aldehydes and KetonesChapter Eleven Aldehydes and Ketones 9. To distinguish of aldehydes

12、and ketone NaHSO3, Tollens reagent，Feling reagent,NaOH + I2常见的鉴别试剂，鉴别对象是什么？Chapter Twelve Carboxylic AcidsFinal ReviewChapter Twelve Carboxylic Acids1. Preparation of Carboxylic Acids选择性氧化Get the carboxylic acid with one more carbon：Chapter Twelve Carboxylic Acids-羟基酸的合成底物的要求？底物的要求？Chapter Twelve Ca

13、rboxylic AcidsGet the carboxylic acid with two more carbon：Iodoform reaction，-unsaturated carboxylic acidChapter Twelve Carboxylic AcidsReformatsky reactionAldol reaction2. Acidity of Carboxylic AcidsChapter Twelve Carboxylic AcidsChapter Twelve Carboxylic AcidsComparing the relative acidity substit

14、uted carboxylic acids12343. Nucleophilic Acyl (酰基 ) Substitution ReactionsChapter Twelve Carboxylic Acids4. Reduction of Carboxylic Acids4. Decarboxylation (脱羧) of Carboxylic AcidsChapter Twelve Carboxylic Acids什么样的羧酸容易脱羧？4. Heating Reactions of Dicarboxylic AcidsChapter Twelve Carboxylic AcidsDecar

15、boxylationIntramolecular dehydration两个羧基相对位置不同，产物不同5. Halogenation of Carboxylic AcidsChapter Twelve Carboxylic Acids-NH2, -CN, -OHmultifunctional molecules X6. Dehydration of Hydroxyl Carboxylic Acids (羟基酸) :Chapter Twelve Carboxylic Acids羟基和羧基的相对位置决定了产物！Chapter Twelve Carboxylic Acids7. Spectrosco

16、py of carboxylic acidsIR:Stretch：1710 cm-1Stretch：3000-2500 cm-11H NMR: = 1013 ppm= 22.5 ppm8. Mechanism:Esterification with acid as catalystChapter Thirteen Carboxylic Acids DerivativesFinal Review1. Nucleophilic Acyl Substitution ReactionAddition reactionElimination reactionRelative reactivity of

17、Nucleophilic Acyl Substitution Reaction:Acid halides Acid anhydride Esters AmidesChapter Thirteen Carboxylic Acids DerivativesHydrolysis, 水解Acoholysis, 醇解PyridineAminolysis, 氨解R2CuLi ?Chapter Thirteen Carboxylic Acids DerivativesChapter Thirteen Carboxylic Acids DerivativesNot often usedEither by aq

18、ueous base or by aqueous acid.Try to propose the mechanism常用来合成连有两个相同取代基的叔醇Chapter Thirteen Carboxylic Acids Derivatives2. The Reduction Reaction of Carboxylic Acids DerivativesLiAlH4 / H3O+ROH3. Chemistry of amides4. Spectroscopy of Carboxylic Acid DerivativesChapter Thirteen Carboxylic Acids Deriv

19、ativesExample Formula Infrared absorption (cm-1)Acetyl chloride CH3COCl 1810Acetyl anhydride (CH3CO) 2O 1820Ethyl acetate CH3COO CH2CH3 1735Acetamide CH3CONH2 1690Acetic acid CH3COOH 1710Acetone CH3COCH3 1715Chapter Thirteen Carboxylic Acids Derivatives1HNMR (ppm)Chapter Fourteen - Keto EstersFinal

20、ReviewChapter Fourteen - Keto Esters1. Claisen condensation reaction酯分子中-氢的酸性-碳负离子的生成-酮酸酯碱亲核取代烷氧基离去Mechanism ?Two step: (1)EtONa/EtOH, (2) H+The mixed Claisen CondensationThe Dieckmann CyclizationMixed Claisen-like reactions-diketones 2. The Acetoacetic Ester(乙酰乙酸乙酯) SynthesisChapter Fourteen - Keto

21、 EstersThese three carbons from acetoacetic esterThis R group from alkyl halide1) NaH / RCOCl; 2) H3O+, heat1) EtONa / RX; 2) EtONa / RX ; 3) H3O+, heat（为引入烷基）（为引入酰基基）反应条件写完整！合成甲基酮在哪里拆分？3. The Malonic Ester (丙二酸酯) SynthesisChapter Fourteen - Keto Esters取代乙酸，在哪里拆分？To prepare1) EtONa / RX; 2) EtONa /

22、RX ; 3) H3O+, heat（为引入烷基）The Knoevenagel ReactionThe Perkin ReactionThe Michael ReactionThe Robinson annulation (环化)- Michael reaction + intramolecular Aldol reaction. Chapter Fourteen - Keto Esters含有活性氢的化合物，在EtONa/EtOH条件下容易失去活性H，产生C-离子中间体，是亲核的质点，会和另外分子的醛酮发生亲核加成，和羧酸的衍生物（酯）发生亲核取代或和，不饱和化合物发生加成。这里考点比较多

23、，大家关注！Final ReviewChapter Fifteen Nitro Compounds and Amines1. Aromatic Nitro CompoundsH2 / Ni ?a) Electrophilic substitution reaction : b) Nucleophilic substitution reaction : Chapter Fifteen Nitro Compounds and Amines2. Synthesis of AminesChapter Fifteen Nitro Compounds and Aminesa. Reduction reac

24、tion :(b) Gabriel amine synthesisChapter Fifteen Nitro Compounds and Amines(c). Reductive Amination of Aldehydes and Ketones(d). Hofmann Rearrangement3. Chemical Properties of Amines(1) . Basicity of AminesThe density of the lone pair electron B A D CTo purify and separate aminesComparing the relati

25、ve basicity:会完成反应Chapter Fifteen Nitro Compounds and Aminesa). 分离，提纯-b). 鉴定和氨基的保护-c). 降低氨基的定位活性，一般只在对位引入取代基(2). Acylation (酰基化) of AminesAmino group NH2-AcylationAmido group RCONH-(3). Sulfonamides (磺酰胺) formationHinsberg Test: To distinguish primary , secondary and tertiary amines 试剂： PhSO2Cl + NaOH不同胺的现象？(4). Electrophilic Aromatic Substitution ReactionChapter Fifteen Nitro Compounds and Aminesa). 胺基容易被氧