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1、REVIEW答疑时间：7月2日15点至17点30分地 点：医基楼化学实验室1有机化学五年制复习(class)我们至少要我们至少要考考60分！分！2有机化学五年制复习(class)It is a shame to cheat in examination 3有机化学五年制复习(class)考试重点及试题分数分布考试重点及试题分数分布一、命名（5小题，每小题1分，共5分）二、选择题（单选题，25小题，每小题1分，共25分）三、完成下列反应式（30小题，每小题2分，共60分）四、鉴别题（1小题，5分）五、推测结构题（1小题，5分）4有机化学五年制复习(class)不列入考试范围的章节：不列入考试范围
2、的章节：第一章 结论第十三章 有机波谱学基础第十四章 杂环化合物和维生素第十八章 核酸第十九章 代谢途径中的辅酶5有机化学五年制复习(class)第二章：烷烃和环烷烃Name ofConformerWedge-HatchedBond StructureSawhorseStructureNewmanProjection6有机化学五年制复习(class)7有机化学五年制复习(class). Stability of radicals: CH3CH3 C CH3CH3CHCH3CH3CH2CH3The radical is more steady, and more easy to be forme
3、d.8有机化学五年制复习(class)P.31 2-12 自由基稳定性： 教科书印刷错误9有机化学五年制复习(class). Chemical properties of alicyclic hydrocarbon1) addition of hydrogenH2 , cat.CH3CH2CH3CH3CH2CH2CH3H2 , cat.high temp.CH3(CH2)3CH3CH3(CH2)4CH310有机化学五年制复习(class)2) react with halogensBr2BrCH2CH2CH2BrBr2BrCH2CH2CH2CH2BrBr2 , hBrBr2 , hBraddi
4、tion:substitution:11有机化学五年制复习(class)HX3) addition of hydrogen halidesHX12有机化学五年制复习(class)Stability of cycloalkanes: Anhydrides Esters Acidamides146有机化学五年制复习(class)147有机化学五年制复习(class)(4) Biuret Reaction (缩二脲反应) Biuret can dissolve in alkali solution. If a little cupric sulfate be added to the biuret
5、alkali solution, the color of the solution will turn to violet color. This color reaction is called Biuret Reaction. Compounds contain two or more than two peptide linkages ( 肽键 ) such as polypeptide, protein, etc. can take place biuret reaction.148有机化学五年制复习(class)完成下列反应式，写出主要产物149有机化学五年制复习(class)15
6、0有机化学五年制复习(class)151有机化学五年制复习(class)152有机化学五年制复习(class)用化学方法鉴别下列各组化合物（1）乙酸乙酯、-丁酮酸、丁酰胺 A B CABCNaHCO3不产生CO2ACBHNO2产生N2C不产生N2A产生CO2153有机化学五年制复习(class)（2）乙酐、甲酸甲酯、乙酰溴 A B CABCAgNO3产生浅黄色沉淀ABCAg(NH3)2NO3产生银镜B不产生银镜A不产生浅黄色沉淀154有机化学五年制复习(class) 化合物A在酸性水溶液中加热，生成化合物B（ C5H10O3）B与NaHCO3反应放出无色气体，与CrO3作用生成C （ C5H8
7、O4），B在室温条件下不稳定，易失水生成A。试写出A，B，C的结构式。解：化合物B的不饱和度为：= = 1 25 + 2 102B在室温条件下不稳定，易失水生成AB为-羟基酸；A为-内酯155有机化学五年制复习(class) A B C156有机化学五年制复习(class)第十二章：胺和生物碱Sequence of the basicity of aminesquaternary ammonium saltquaternary ammonium hydratetertiary amine157有机化学五年制复习(class)2. Acylationamide 158有机化学五年制复习(clas
8、s)3. Sulfonylationbenzene sulfonyl chloridep-toluenesulfonyl chloride-I effectweak acidcrystalbenzene sulfonamide159有机化学五年制复习(class)The above reaction is named Hinsberg Reaction. Using this reaction can distinguish primary, secondary and tertiary amines. The products of primary amines react with ben
9、zene sulfonyl chloride is weak acid, so can dissolve in sodium hydroxide solution. The products of secondary amines are crystal, and can not dissolve in sodium hydroxide solution. For tertiary amines, this reaction can not take place.160有机化学五年制复习(class)4. React with nitrous acid (HNO2)(1) Primary am
10、ines161有机化学五年制复习(class)(2) Secondary amines(3) Tertiary aminesAliphatic tertiary amines do not react with nitrous acid to give an isolable product.nitrosoamines (yellow oil)162有机化学五年制复习(class)yellow solidActually, we use sodium nitrite/hydrochloric acid NaNO2/HCl instead of nitrous acid (HNO2).163有机
11、化学五年制复习(class)Section 2 Diazo and Azo Compounds. Diazotization Reactionbenzene diazonium chloride. Reaction of Diazo Salt1. Substitution05164有机化学五年制复习(class)165有机化学五年制复习(class)H3PO2: hypophosphorous acid (次磷酸次磷酸)166有机化学五年制复习(class)2) How to synthesize 1,3,5-tribromobenzene from benzene?Question: 1)
12、How to synthesize 2-methyl benzoic acid from toluene?167有机化学五年制复习(class)051)168有机化学五年制复习(class)2)05169有机化学五年制复习(class)2. Coupled ReactionHOAc, NaOAc170有机化学五年制复习(class)2. Hydrolysis171有机化学五年制复习(class)(4) Biuret Reaction (缩二脲反应) Biuret can dissolve in alkali solution. If a little cupric sulfate be add
13、ed to the biuret alkali solution, the color of the solution will turn to violet color. This color reaction is called Biuret Reaction. Compounds contain two or more than two peptide linkages ( 肽键 ) such as polypeptide, protein, etc. can take place biuret reaction.172有机化学五年制复习(class)第十五章：糖类Almost natu
14、ral sugars are D sugars.173有机化学五年制复习(class)Oligosaccharides and polysaccharides can be hydrolyzed to monosaccharides, so all sugars have a reaction as follow:saccharidesconc. H+-H2Oviolet compoundThis reaction is named as Molisch reaction, can be used to distinguish saccharides.174有机化学五年制复习(class).
15、Oxidation monosaccharides Ag + complex productsTollens reagent1. React with Tollens, Fehlings or Benedicts reagentmonosaccharides Cu2O + complex productsFehlings or Benedicts reagent(brick red color)175有机化学五年制复习(class)Cause: all monosaccharides (include ketoses) can react with Tollens, Fehlings and
16、Benedicts reagent. Reducing sugar: a sugar can react with Tollens, Fehlings and Benedicts reagent. In other words, reducing sugar contain some amount of an oxidizable free aldehyde group. Reducing sugars endow with mutarotation.Nonreducing sugar: a sugar can not react with Tollens, Fehlings and Bene
17、dicts reagent. Nonreducing sugars do not endow with mutarotation.176有机化学五年制复习(class)Glycosides are not Reducing SugarsGlycosides lacks a free hemiacetal function; cannot be in equilibrium with a species having an aldehyde function.177有机化学五年制复习(class)2. React with BromineBromine in water is a mild ox
18、idant, it converts only the aldehyde into a carboxylic acid, the primary and secondary hydroxyls are not touched, and the product is called an aldonic acid.aldonic acid178有机化学五年制复习(class)D-galactoseD-galactaric acid or mucic acidQuestion: Is D-galactaric acid a chiral molecule? why?D-galactaric acid
19、 is not a chiral molecule, because the molecule contain a plane of symmetry. It is a meso compound.179有机化学五年制复习(class)180有机化学五年制复习(class)sucrose (table sugar)181有机化学五年制复习(class) -1，4-glycosidic linkagemaltose, 麦芽糖 -D-glucopyranoseD-glucose182有机化学五年制复习(class)1. Amylose (直链淀粉, 糖淀粉) -1，4-glycosidic lin
20、kage183有机化学五年制复习(class)2. Amylopectin (支链淀粉,胶淀粉) -1，4-glycosidic linkage -1，6-glycosidic linkage184有机化学五年制复习(class)Iodine is used to distinguish starch. Put the iodine to the solution of starch, the solution show blue color.185有机化学五年制复习(class)Br2/H2O用简便方法区别下列各组化合物（1）葡萄糖和果糖ABAB红棕色消失不褪色AB186有机化学五年制复习(
21、class)托伦试剂（2）葡萄糖和蔗糖ABAB产生银镜反应不产生银镜反应AB187有机化学五年制复习(class)I2（3）蔗糖和淀粉ABAB不显蓝紫色显蓝紫色AB188有机化学五年制复习(class)托伦试剂（4）甲基-D-吡喃葡萄糖苷和2-O- D-吡喃葡萄糖苷ABAB不产生银镜反应产生银镜反应AB189有机化学五年制复习(class)写出D-(+)-半乳糖与下列试剂反应的主要产物190有机化学五年制复习(class)191有机化学五年制复习(class)192有机化学五年制复习(class)第十六章：脂类linoleic acid, -linolenic acid and arachid
22、onic acid are essential fatty acids. Essential fatty acids: essential in our diets because our bodies cannot make them, yet use them to make many other fatty acids our bodies must have. 193有机化学五年制复习(class)Saponification number: The amount (mg) of KOH that can hydrolyze 1g oils and fats completely.We
23、 can use the saponification number to deduce the average molecular weight of oils and fats approximately. saponification numberaverage molecular weightcontent of low molecular weight oils and fatslarge smallsmall largehigh low194有机化学五年制复习(class)(2) Addition of iodineIodine number: the amount of iodi
24、ne (g) which be absorbed by 100g oils and fats.Iodine number can be used to deduce the unsaturated degree of oils and fats.iodine numberunsaturated degreelarge smallhigh low195有机化学五年制复习(class)Acidic number: the amount (mg) of KOH which can neutralize the dissociated fatty acids of 1g oils and fats.a
25、cidic numberdissociated fatty acidthe degree of ranciditylarge smallmore lesslarge small196有机化学五年制复习(class)5-steroidsSubstituents point either down (dashed bond, ) or up (solid bond, )197有机化学五年制复习(class)5-steroids198有机化学五年制复习(class)ultravioletVitamin D37-dehydrocholesterolultravioletergosterol麦角甾醇Vi
26、tamin D2199有机化学五年制复习(class)第十七章：氨基酸、多肽和蛋白质Almost nature amino acids are L-amino acids.All 20 of the amino acids are necessary for protein synthesis. Our body can synthesize more than one-half of these 20 amino acids from starting materials provided by the food. But there are nine or ten are unable t
27、o make in our body, which are called essential amino acids.200有机化学五年制复习(class)valine, Val, Vleucine, Leu, Lthreonine, Thr, Tisoleucine, Ile, I缬氨酸亮氨酸异亮氨酸苏氨酸201有机化学五年制复习(class)methionine, Met, Mlysine, Lys, Kphenylalanine, Phe, Ftryptophan, Try, W (necessary for synthesis of tyrosine) (necessary for s
28、ynthesis of cysteine )蛋氨酸赖氨酸苯丙氨酸色氨酸202有机化学五年制复习(class)The following amino acids are also essential amino acids:histidine, His, T necessary only for infants203有机化学五年制复习(class)arginine, Arg, R necessary only for cats204有机化学五年制复习(class)pHpIformuladirection of electrophoresis cathode no movement anodech
29、arge state + / 205有机化学五年制复习(class)5. React with nitrous acid (HNO2)What difference between nitrous acid react with amino acids and nitrous acid react with aliphatic amines?206有机化学五年制复习(class)8. React with ninhydrinAmino acids react with ninhydrin to form a deep purple molecule, Ruhemanns purple. It
30、is this purple color that is used to detect amino acids except proline, regardless of the identify of the R group, form the same purple molecule on reaction with ninhydrin.Ruhemanns purple207有机化学五年制复习(class)Chemical bonds of proteins:1. Principal bond (主键主键): peptide linkage2. Auxiliary bonds (副键副键)
31、:(1) Hydrogen bondbetween main chainsbetween main chain and side chainbetween side chains208有机化学五年制复习(class)(2) Disulfide bondmercaptan209有机化学五年制复习(class)Thiols in adjacent chains can form a disulfide RSSR through spontaneous oxidation.A disulfide bond between cysteine residues in different peptide
32、chains links the otherwise separate chains together, while a disulfide bond between cysteine residues in the same chain forms a loop. 210有机化学五年制复习(class)(3) Hydrophobic bond: The nonpolar, “greasy” hydrophobic hydrocarbon portions cluster inside the molecule, maximally protected from the hostile aqu
33、eous environment.211有机化学五年制复习(class)(5) Salt bond (ionic bond)(6) Coordinate bond(4) Van der Waals force212有机化学五年制复习(class)Primary structure: the sequence of amino acids in a protein.213有机化学五年制复习(class)Secondary structure: ordered regions of a protein chain. The two most common types of secondary st
34、ructure are the -helix and the -pleated sheet.214有机化学五年制复习(class)2. PrecipitationTwo main factors for stability of proteins solution:a. electric charge; b. hydration shellIf we can destroy one or two stable factors, the proteins will precipitate from the solution.(1) Salting outThe leading effect of
35、 salting out is destroying the hydration shell. (NH4)2SO4 is the common reagent.215有机化学五年制复习(class)(2) Organic solventMethanol, ethanol and acetone can be used to destroy hydration shell and cause precipitation of proteins.(3) Heavy metal saltsAdjusting the pH of the solution until pHpI, then heavy
36、metal salts be added to precipitate proteins.216有机化学五年制复习(class)(4) Alkaloidal reagentsAdjusting the pH of the solution until pHpI, then alkaloidal reagents be added to precipitate proteins.217有机化学五年制复习(class)(5) Antibody-antigen reaction.218有机化学五年制复习(class)3. Denaturation: The destructure of the hi
37、gher order structure of a protein (not involve with primary structure), sometimes reversible, sometimes not.219有机化学五年制复习(class)PROTEIN DENATURATIONPhysical:HeatingCoolingMechanical treatmentHydrostatic pressure RadiationChemical:AcidsBasesMetals Organic solvents220有机化学五年制复习(class)4. Color reactions:(1) biuret reaction(2) react with ninhydrin(3) react with nitric acid221有机化学五年制复习(class)22217-6. 写出下列反应中的反应产物有机化学五年制复习(class)223cystinehistamine有机化学五年制复习(class) 祝各位亲与 “考神” 同在：逢考必过逢考必过有机化学五年制复习(class)
