Seeking organic summary of chemistry in senior one.

First, the nature of functional groups.

1. Inferring the structure of functional groups according to the properties of organic substances.

(1) The substances that can undergo an addition reaction are C = C or C ≡ C≡C (-CHO and-C6H5 can generally only undergo an addition reaction with H2).

⑵ Substances that can react with silver mirror or generate red precipitate with newly prepared Cu(OH)2 suspension must contain-CHO. Aldehyde can be oxidized to carboxylic acid and reduced to alcohol; It is carboxylic acid that can dissolve Cu(OH)2 at room temperature. It is carboxylic acid that turns red when encountering litmus test solution.

(3) Substances that can react with active metals such as sodium and magnesium to generate H2 contain -OH or-COOH.

(4) The substance that can react with Na2CO3 and NaHCO3 solution to generate CO2 contains-COOH.

5] Phenol is released when it reacts with a small amount of Na2CO3 solution without CO2 gas;

[6] Phenol, carboxylic acid, ester or halogenated hydrocarbon react with NaOH solution;

Once the alcohol can be oxidized to carboxylic acid, it must contain the structure of "─CH2OH" (the alcohol that can be oxidized, the "even" carbon atom of hydroxyl phase contains hydrogen atom; Alcohol that can undergo elimination reaction, and the "O" carbon atom of hydroxyl phase contains hydrogen atom);

(8) The hydrolyzable organic compounds are esters, halogenated hydrocarbons, disaccharides and polysaccharides, peptide bonds and protein;

(9) Substances that can be hydrolyzed into alcohols and carboxylic acids contain ester groups-Chief Operating Officer-;

⑽ The purple substance that reacts with FeCl3 _ 3 solution is phenol;

⑾ The substance that can undergo elimination reaction contains or (for example, X stands for halogen atom).

2. Infer the number of functional groups according to the properties and related data.

Reaction of (1) with X2, h X and H2: substitution of (H ~ X2); Addition (c ═ c ~ x2 or HX or H2; C ≡ C≡C~2X2 or 2HX or 2H2；; -C6H5 ~3H2)

⑵ silver mirror reaction: r-CHO ~ 2ag;

(3) reacting with newly prepared Cu(OH)2: R-CHO ~ 2cu (OH) 2; R─COOH~ 1/2Cu(OH)2

⑷ reaction with sodium: R-OH ~ 1/2h2.

5) reacting with NaOH: phenolic hydroxyl group ~ NaOH and a carboxyl group ~ ~ NaOH；; An alcohol ester ~ ~ NaOH；; Monophenol ester ~ 2 NaOHr─X ~ NaOH；; C 6 H 5-X 2 sodium hydroxide.

[6] Reaction with CO32: 2-COOH ~ CO32-~ CO2 =

(7) Reaction with HCO3: -COOH ~ HCO3-~ CO2 =

8 esterification: -cooh ~-oh ~-COO-.

3. Inferring the position of functional groups from some products

(1), it can be determined that -OH must be attached to the C atom with two H atoms, that is, it has the following structure: Similarly, if an alcohol has the following structure: if an alcohol cannot be oxidized, it has the following structure:.

⑵ The position of-OH or -X can be determined by eliminating the reaction products. If the elimination reaction of alcohol or halogenated hydrocarbon produces the following products:, it can be known that -OH or -X must be at the 1 or the 2 nd position of C atom. ..

⑶ The structure of carbon chain can be determined by the number of substituted products. If it is known that the monochloro substituent on the benzene ring of benzene homologue C8H 10 has only one structure, the structural formula of the homologue is, if there are two, or there are three.

4. Transformation diagram between hydrocarbons and hydrocarbon derivatives

Secondly, the types of organic reactions are summarized.

1. substitution reaction: a reaction in which some atoms or atomic groups in organic molecules are replaced by other atoms or atomic groups.

(1) halogenation: the reaction in which hydrogen atoms in organic molecules are replaced by halogen atoms.

⑵ Nitrification reaction: the reaction in which hydrogen atoms in organic molecules are replaced by nitro groups.

(3) Others: hydrolysis and esterification of halogenated hydrocarbons, hydrolysis of esters, intermolecular dehydration of alcohols, etc. It is also a substitution reaction.

2. Addition reaction: A reaction in which unsaturated carbon atoms in organic molecules directly combine with other atoms or atomic groups to form new substances.

Addition reaction (reduction) of (1) with hydrogen: under the action of catalyst, organic matter containing unsaturated carbon atoms reacts with hydrogen: (1) catalytic hydrogenation of olefins, dienes and alkynes; ② Catalytic hydrogenation of benzene, benzene homologues and styrene; ③ Catalytic hydrogenation of aldehydes and ketones; ④ Hydrogenation hardening of oil.

⑵ Addition reaction with halogen: organic compounds with C=C and C≡C bond can easily react with halogen.

⑶ Addition reaction with hydrogen halide: organic compounds with C=C and C≡C bond can react with hydrogen halide. For example: acetylene → vinyl chloride.

⑷ Addition reaction with water: organic compounds with C=C and C≡C bond can react with water under the action of catalyst. For example, olefins are hydrated to produce alcohols.

3. Dehydration reaction: the reaction of removing hydrogen and oxygen equivalent to water from organic matter under appropriate conditions. Such as alcohol dehydration.

(1) intramolecular dehydration (elimination reaction): C-OH bonds and C-H bonds on carbon atoms adjacent to hydroxyl groups are broken, and water molecules are eliminated to form unsaturated bonds.

⑵ Intermolecular dehydration: the C-O bond in one alcohol molecule is broken, and the O-H bond in another alcohol molecule is broken, and dehydration generates ether. The alcohols participating in the reaction may be the same or different, and may be monohydric alcohols or polyhydric alcohols. Dehydration of methanol and ethanol can form three kinds of ethers.

4. Elimination reaction: the reaction of organic matter to eliminate small molecules (such as water, HX, etc.). Under appropriate conditions, unsaturated (double bond or triple bond) compounds are generated from one molecule.

(1) Eliminate alcohol: for example, make ethylene in the laboratory.

(2) Elimination reaction of halogenated hydrocarbons: for example, ethylene is obtained by eliminating chloroethane in sodium hydroxide alcohol solution.

5. Hydrolysis reaction

The common types are: hydrolysis of halogenated hydrocarbon, hydrolysis of ester, hydrolysis of oil (including saponification), hydrolysis of sugar, hydrolysis of peptide and protein, etc.

6. Oxidation reaction: refers to the reaction of adding oxygen or removing hydrogen to organic matter. Reaction of alcohols, carboxylic acids, phenols, etc. Although the active metal is dehydrogenated, it is still reduced)

⑴ Alcohol is oxidized: O-H bond of hydroxyl group is broken, and C-H bond of carbon atom connected with hydroxyl group is broken, and hydrogen atom is removed to form C = O bond. Tertiary alcohols (there is no H on the carbon atom where the hydroxyl group is located) cannot be oxidized.

⑵ Aldehyde is oxidized: the C-H bond of aldehyde group is broken, and aldehyde group is oxidized to carboxyl group:.

⑶ Ethylene oxidation: 2ch2 = 2CH2=CH2+O22CH3CHO

⑷ The burning of organic matter, unsaturated hydrocarbon homologues and benzene makes the acidic KMnO4 solution fade.

5. Reactions of aldehydes and compounds containing aldehyde groups with newly prepared alkaline copper hydroxide or silver ammonia solution.

[6] When placed in the air, phenol is converted into a pink substance (quinone).

7. Reduction reaction: refers to the reaction of hydrogenation or deoxidation of organic matter.

Catalytic hydrogenation of (1) aldehydes, ketones, olefins, alkynes, benzene and its homologues, phenols, unsaturated oils, etc.

⑵

8. Esterification reaction: the reaction of acid and alcohol to form ester and water.

Such as: making ethyl acetate, ethyl nitrate, nitrocellulose, cellulose acetate, nitroglycerin, etc.

Law: dehydroxylation of organic acids, that is, the C-O bond in hydroxyl groups is broken; Dehydrogenation of alcohol, that is, the O-H bond in hydroxyl group breaks to form ester and water.

9. Polymerization: refers to the reaction in which small molecules react with each other to form polymers.

(1) addition polymerization: the reaction of addition polymerization of unsaturated monomers into polymer compounds. The reaction is completed by self-polymerization or * * * polymerization of monomers.

⑵ Polycondensation: refers to the reaction between monomers, which produces macromolecules and micromolecules at the same time. The monomers of this kind of reaction generally have two or more functional groups or active hydrogen. Such as phenolic resin, amino acid forming protein, etc.

10. Cracking reaction: Under certain conditions, long-chain hydrocarbons with high molecular weight and high boiling point are cracked into short-chain hydrocarbons with low molecular weight and low boiling point. Cracking is a chemical process. Such as C16H34C8h18+C8h16, deep cracking is called cracking.

1 1. color reaction (color reaction)

(1) phenol solution with ferric chloride solution-purple.

Starch solution and iodine water-blue.

(3) protein (with benzene ring in its molecule) is yellow with concentrated nitric acid.

thoughtway

In the school-based curriculum, photography is one of the subjects often taught. Mi Tuer is a commonly used acute chromogenic agent, and its structural formula is

The following statement about organic matter is correct.

A. Mi Tuer belongs to amino acids.

B. Under certain conditions, 1 mol can react with 2 mol NaOH at most.

C Mi Tuer can be converted into alcohols by one-step reaction.

Mi Tuer can decolorize bromine water, but not acidic potassium permanganate.

According to the analysis, Mi Tuer molecule has no carboxyl group and is not an amino acid. According to its structure, the molecule belongs to sulfate. Because the phenolic hydroxyl group in the molecule can react with alkali, the salt formed by amino group can also react with alkali. So 1 mole can react with 4 moles of NaOH at most, and both A and B are wrong. When phenyl in Mi Tuer molecule is hydrogenated to cyclohexyl, the product can be regarded as alcohol, and C is correct. Phenolic hydroxyl can discolor both bromine water and acidic potassium permanganate, and D is wrong. This question should be C.

Silicone rubber is a kind of high temperature resistant rubber, which is formed by two reactions of dimethyldichlorosilane.

Into a polymer compound:

HOH

Among them, the product obtained in reaction A can be regarded as a dimethyl substitute of unstable orthosilicic acid (H4SiO4), which can be dehydrated to form more stable silicic acid. The following statement is incorrect.

A as can be seen from the above, the chemical formula of n-carbonic acid is h4co4b. HC (oc2h5) 3 can be named triethyl orthoformate.

C. the types of reactions a and b belong to substitution reaction d, but the types of reactions a and b do not belong to substitution reaction.

By analyzing the dehydration of orthosilicic acid (losing two hydroxyl groups and forming a carbonyl group) to form silicic acid, it can be inferred that the chemical formula of orthosilicic acid is H4CO4 from the chemical formula of carbonic acid, and option A is correct. The structural abbreviation of formic acid is HCOOH. Obviously, the carbonyl group in formic acid molecule is formed by dehydration of two hydroxyl groups in orthoformic acid molecule. Therefore, the structural abbreviation of orthoformic acid is HC(OH)3, and the acid molecule contains three hydroxyl groups, which can be esterified with ethanol to produce HC(OC2H5)3. According to the naming rules of ester, the ester should be named triethyl orthoformate, and option B is correct. For options C and D, according to the reaction, reaction A belongs to the hydrolysis reaction of halogenated hydrocarbons, which can also be called substitution reaction, and reaction B can be regarded as the process of forming ether chains by hydroxyl groups, in which small molecular water is generated, which is a polycondensation reaction and a substitution reaction. You should choose D for this question.

Example 3 It is impossible to identify the following reagent groups with only one reagent.

A. Solutions of methanol, formaldehyde and formic acid B. Three solutions of benzene, phenol and styrene

C. Three liquids: benzene, bromobenzene and ethanol D. Three liquids: benzene, hexene and hexane.

Analysis option A can be identified by newly produced copper oxide, which is dissolved in formic acid solution when it is not heated and generates brick red precipitate when it is heated. In option b, bromine water can be used for identification. Phenol and bromine water will produce white precipitate, and styrene will react with bromine water to make bromine water fade. Option c can be identified by water: benzene is the upper organic matter, bromobenzene is the lower organic matter, and ethanol is miscible with water; In option D, only bromine water or KMnO4 solution can be added to identify hexene, but benzene and hexane cannot be identified. You should choose D for this question.

Example 4 The interrelationships of organic substances A, B, C, D, E, E and G are shown in the following figure. 5.2g F can be mixed with 100mL 1mol? L- 1 NaOH solution is just completely neutralized, and 0. 1mol F can react with enough metal sodium to release 2.24L H2 under standard conditions. The molecular formula of D is C3H3O2Na, and the molecule of E contains carboxyl groups.

(1) Write the structural formula of the following substances: g; f .

⑵ Chemical reaction type: ①; ④ 。

⑶ Chemical equation: ①; ③ 。

According to the analysis, "5.2g F can match 100mL 1mol? L- 1 NaOH solution is just completely neutralized, and 0. 1mol F can react with enough metal sodium to release 2.24L H2 "as dicarboxylic acid under standard conditions, assuming its molar mass is M g? Mol- 1, right, m = 104g? Mol- 1. Because the molecule of A contains six C atoms and the molecular formula of D is C3H3O2Na, it is known that B, C, E, F and G all contain only three carbon atoms. According to f, the molar mass is 104 g? From the dicarboxylic acid with the molar number of 1, it can be concluded that the structural formula of F is hooc-CH2-cooh, and then G is Ho-CH2 CH2 CH2-OH. By combining D and G, A is CH2 = CH2 = CH2=CH-COOCH2CH2CH2Br, then B is CH2 = CH2=CH-COONa, C is BRCH2CH2 OH, and E is hooc. The answer is: (1) g: ho-ch2ch2-ohf: hooc-CH2-cooh.

(2) ① Elimination reaction ④ Substitution (hydrolysis) reaction

⑷①Br-ch2ch 2-COOH+2 nao HCH 2 = CH-COONa+NaBr+2H2O

③CH2 = CH-cooch 2ch2 CH 2cr+H2 och 2 = CH-COOH+br CH 2ch2 CH 2 oh

Example 5 A, B, C, D, E, F, G and H in the figure below are all organic compounds.

Answer the following questions:

(1) If the relative molecular weight of organic compound A is less than 60, A can react with silver mirror, and 1 mol A can react with 3 mol H2 under the action of catalyst to generate B, Then the structural formula of A is _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _

(2) B can be heated in concentrated sulfuric acid to generate C, and C can be polymerized to generate polymer compound D under the action of catalyst. The chemical equation for generating D from C is _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _;

(3) The molecular formula of (1) aromatic compound E is C8H8Cl2. There is only one bromine substituent on the benzene ring of E, then all possible structural formulas of E are _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _

②E can be transformed into F in NaOH solution, and F is oxidized to G(C8H6O4) by potassium permanganate acid solution. 1 mol G reacts with a sufficient amount of NaHCO3 solution, and 44.8 L CO2 CO2 can be released (under standard conditions), from which the structural formula of e is determined to be _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _.

(4) H can be generated by heating G and enough B under the catalysis of concentrated sulfuric acid, so the chemical equation of H generated by G and B is:

_ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _

Analysis of (1) A can produce a silver mirror reaction, indicating that A contains-CHO; While 1 mol aldehyde group can react with 1 mol H2, but 1 mol A can react with 3 mol H2 under the action of catalyst, indicating that there are still two unsaturations in the molecule. Now Mr(-CHO) = 29, and Mr (a) < 60, so A should contain an alkynyl group, and A is HC ?.

⑵ b (ch3ch2oh) undergoes elimination reaction under the action of concentrated sulfuric acid to generate c, and c is CH3CH═CH2, and propylene can undergo addition polymerization to generate d (polypropylene).

(3) The molecular formula of ① e is C8H8Cl2. There is only one bromine substituent on the benzene ring of e, which shows that the molecular structure of e is very symmetrical, and then all possible structural simplification of e is deduced. ②E can be converted into F in NaOH solution, indicating that chlorine atom has been hydrolyzed to -OH. After F is oxidized by KMnO4, the product G(C8H6O4) 1 mol and enough NaHCO3 can release 2mol CO2, indicating that G contains 2 -COOH, and the benzene ring will not contain oxygen atoms, so the chlorine atom in E should not be attached to the benzene ring, that is, E should be hydroquinone, and the property of G can be determined as. (Note: If we consider the hydrolysis of halogen atoms on benzene ring, firstly, the hydrolysis conditions are very harsh, and secondly, the phenol generated after hydrolysis is oxidized by acidic potassium permanganate solution, and the benzene ring structure is destroyed, so it is impossible to generate dicarboxylic acids). The answer is:

⑴HC≡C-CHO； Addition reaction (or reduction reaction) 2 2 ⑵nCH3CH═CH2

⑶①、、、、、、。 ②。

⑷+2CH3CH2CH2OH+2H2O .

Esterification reaction (or substitution reaction)