Chemical properties of organic substances in schemes. Student's Handbook of Organic Chemistry
SIBERIAN POLYTECHNICAL COLLEGE
STUDENT HANDBOOK
in ORGANIC CHEMISTRY
for specialties of technical and economic profiles
Compiled by: teacher
2012
Structure "STUDENT'S HANDBOOK on ORGANIC CHEMISTRY"
EXPLANATORY NOTE
The SS in organic chemistry is designed to assist students in creating a scientific picture of the world through chemical content, taking into account interdisciplinary and intradisciplinary connections, the logic of the educational process.
The SS in organic chemistry presents the minimum in terms of volume, but functionally complete content for the development of the state standard chemical education.
The CC in Organic Chemistry performs two main functions:
I. The information function allows participants in the educational process to get an idea of the content, structure of the subject, the relationship of concepts through diagrams, tables and algorithms.
II. The organizational and planning function provides for the allocation of training stages, the structuring of educational material, and creates ideas about the content of the intermediate and final certification.
SS involves the formation of a system of knowledge, skills and methods of activity, develops the ability of students to work with reference materials.
Name | Name |
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Chronological table "Development of organic chemistry". | Chemical properties of alkenes (ethylene hydrocarbons). |
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The main provisions of the theory of the structure of organic compounds | Chemical properties of alkynes (acetylenic hydrocarbons). |
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Isomers and homologues. | Chemical properties of arenes (aromatic hydrocarbons). |
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TSOS value | |||
Classification of hydrocarbons. | Genetic connection of organic substances. |
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homologous series ALKANE (LIMITED HYDROCARBONS). | Relationship "Structure - properties - application". |
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homologous series RADICALS FORMATED FROM ALKANE. | Relative molecular weights of organic substances |
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Dictionary of terms in organic chemistry. nominal reactions. |
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Isomerism of classes of organic substances. | Algorithm for solving problems. Physical quantities for solving problems. |
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Chemical properties of alkanes (saturated hydrocarbons). | Derivation of compound formulas. Examples of problem solving. |
CHRONOLOGICAL TABLE "DEVELOPMENT OF ORGANIC CHEMISTRY"
Period/year. Who? | The nature of the discovery |
|
Ancient Shih | ancient man | Boil food, tan leather, make medicine |
Paracelsus and others | The manufacture of more complex drugs, the study of the properties of substances org. origin, i.e. waste products |
|
XY-XYIII c. in. | Continuous process | Accumulation of knowledge about various substances. The supremacy of "VITALISTIC VIEWS" |
An explosion of scientific thought, the detonator of which was the needs of people for dyes, clothes, food. |
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Jöns Jakob Berzelius (Swedish chemist) | The term "organic chemistry" |
|
Friedrich Wöhler (German) | Synthesis of oxalic acid |
|
concept | Organic chemistry is a branch of chemical science that studies carbon compounds. |
|
Friedrich Wöhler (German) | Urea synthesis |
|
Synthesis of aniline |
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Adolf Kulbe (German) | Synthesis of acetic acid from carbon |
|
E. Frankland | The concept of "connecting system" - valence |
|
Pierre Berthelot (French) | Synthesized ethyl alcohol by hydration of ethylene. Synthesis of fats. "Chemistry doesn't need life force!" |
|
Synthesis of a sugar substance |
||
Based on various theories (Frankland, Gerard, Kekule, Cooper) created TSOS |
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Textbook "Introduction to the Complete Study of Organic Chemistry". Organic chemistry is the branch of chemistry that studies hydrocarbons and their derivatives. . |
MAIN PROVISIONS
THEORIES OF THE STRUCTURE OF ORGANIC COMPOUNDS
A. M. Butlerova
1. A. in M. are connected in a certain sequence, according to their valency.
2. The properties of substances depend not only on the qualitative and quantitative composition, but also on the chemical structure. Isomers. Isomerism.
3. A. and A. groups mutually influence each other.
4. By the properties of a substance, you can determine the structure, and by the structure - properties.
Isomers and homologues.
Qualitative composition | Quantitative composition | Chemical structure | Chemical properties |
|
Isomers | same | same | various | various |
homologues | same | different | similar | similar |
TSOS value
1. Explained the structure of M. known substances and their properties.
2. Made it possible to foresee the existence of unknown substances and find ways to synthesize them.
3. Explain the diversity of organic substances.
Classification of hydrocarbons.
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homologous series
ALKANE (LIMITED HYDROCARBONS)
Formula | Name |
METHANE |
|
C2H6 | ETHANE |
С3Н8 | PROPANE |
BUTANE |
|
PENTAN |
|
HEXANE |
|
HEPTANE |
|
OCTANE |
|
NONAN |
|
С10Н22 | DEAN |
homologous series
RADICALS FORMATED FROM ALKANE
Formula | Name |
METHYL |
|
C2H5 | ETHYL |
С3Н7 | PROPIL |
BUTYL |
|
PENTIL |
|
HEKSIL |
|
GEPTIL |
|
OKTIL |
|
NONIL |
|
C10H21 | DECYL |
General information about hydrocarbons.
DIV_ADBLOCK54">
Chemical properties of alkanes
(saturated hydrocarbons).
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Chemical properties of alkynes
(acetylenic hydrocarbons).
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Genetic link between hydrocarbons.
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Relationship "Structure - properties - application". | Ways receiving |
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| Structure | ||
Compound | Finding in nature | ||
| Properties | Application |
|
MOLECULAR WEIGHTS OF SOME ORGANIC SUBSTANCES.
Name | ||||||||
Alkanes | ||||||||
Halogen derivatives | ||||||||
Alcohols and Phenols | ||||||||
Ethers | ||||||||
Aldehydes | ||||||||
carboxylic acids | ||||||||
Nitro compounds | ||||||||
Problem solving algorithm
1. Study the conditions of the problem carefully: determine with what quantities the calculations are to be carried out, designate them with letters, set their units of measurement, numerical values, determine which value is the desired one.
2. Write down these tasks in the form of brief conditions.
3. If in the conditions of the problem we are talking about the interaction of substances, write down the equation of the reaction (reactions) and equalize it (their) coefficients.
4. Find out the quantitative relationships between the data of the problem and the desired value. To do this, divide your actions into stages, starting with the question of the problem, finding out the patterns with which you can determine the desired value at the last stage of calculations. If the initial data lacks any values, think about how they can be calculated, i.e., determine the preliminary stages of the calculation. There may be several of these steps.
5. Determine the sequence of all stages of solving the problem, write down the necessary calculation formulas.
6. Substitute the corresponding numerical values of the quantities, check their dimensions, and perform calculations.
Derivation of compound formulas.
This type of calculation is extremely important for chemical practice, since it allows, on the basis of experimental data, to determine the formula of a substance (simple and molecular).
Based on the data of qualitative and quantitative analyzes, the chemist first finds the ratio of atoms in a molecule (or other structural unit of a substance), that is, its simplest formula.
For example, the analysis showed that the substance is a hydrocarbon
CxHy, in which the mass fractions of carbon and hydrogen are respectively equal to 0.8 and 0.2 (80% and 20%). To determine the ratio of atoms of elements, it is enough to determine their amounts of matter (number of moles): Integer numbers (1 and 3) are obtained by dividing the number 0.2 by the number 0.0666. The number 0.0666 will be taken as 1. The number 0.2 is 3 times greater than the number 0.0666. So CH3 is the simplest the formula for this substance. The ratio of C and H atoms, equal to 1:3, corresponds to an innumerable number of formulas: C2H6, C3H9, C4H12, etc., but only one formula from this series is molecular for a given substance, i.e., reflecting the true number of atoms in its molecule. To calculate the molecular formula, in addition to the quantitative composition of a substance, it is necessary to know its molecular weight.
To determine this value, the relative gas density D is often used. So, for the above case, DH2 = 15. Then M(CxHy) = 15µM(H2) = 152 g/mol = 30 g/mol.
Since M(CH3) = 15, it is necessary to double the indices in the formula to match the true molecular weight. Consequently, molecular substance formula: C2H6.
The definition of the formula of a substance depends on the accuracy of mathematical calculations.
When finding a value n element should take into account at least two decimal places and carefully round numbers.
For example, 0.8878 ≈ 0.89, but not 1. The ratio of atoms in a molecule is not always determined by simply dividing the resulting numbers by a smaller number.
by mass fractions of elements.
Task 1. Set the formula of a substance that consists of carbon (w=25%) and aluminum (w=75%).
Divide 2.08 by 2. The resulting number 1.04 does not fit an integer number of times in the number 2.78 (2.78:1.04=2.67:1).
Now let's divide 2.08 by 3.
In this case, the number 0.69 is obtained, which fits exactly 4 times in the number 2.78 and 3 times in the number 2.08.
Therefore, the x and y indices in the AlxCy formula are 4 and 3, respectively.
Answer: Al4C3(aluminum carbide).
Algorithm for finding the chemical formula of a substance
by its density and mass fractions of elements.
A more complex version of the tasks for deriving formulas of compounds is the case when the composition of a substance is given through the combustion products of these.
Task 2. When burning a hydrocarbon weighing 8.316 g, 26.4 g of CO2 was formed. The density of the substance under normal conditions is 1.875 g / ml. Find its molecular formula.
General information about hydrocarbons.
(continuation)
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Natural sources of hydrocarbons.
Oil - fossil, liquid fuel, a complex mixture of organic substances: saturated hydrocarbons, paraffins, naphthenes, aromatics, etc. Oil usually contains oxygen-, sulfur- and nitrogen-containing substances.
Oily liquid with a characteristic odor, dark in color, lighter than water. The most important source of fuel, lubricating oils and other petroleum products. The main (primary) processing process is distillation, as a result of which gasoline, naphtha, kerosene, solar oils, fuel oil, petroleum jelly, paraffin, and tar are obtained. Secondary recycling processes ( cracking, pyrolysis) make it possible to obtain additional liquid fuel, aromatic hydrocarbons (benzene, toluene, etc.), etc.
Petroleum gases - a mixture of various gaseous hydrocarbons dissolved in oil; they are released during extraction and processing. They are used as fuel and chemical raw materials.
Petrol- a colorless or yellowish liquid, consists of a mixture of hydrocarbons ( C5 - C11 ). It is used as motor fuel, solvent, etc.
Naphtha- transparent yellowish liquid, a mixture of liquid hydrocarbons. It is used as diesel fuel, solvent, hydraulic fluid, etc.
Kerosene- transparent, colorless or yellowish liquid with a blue tint. It is used as a fuel for jet engines, for household needs, etc.
Solar- a yellowish liquid. It is used for the production of lubricating oils.
fuel oil– heavy oil fuel, a mixture of paraffins. They are used in the production of oils, fuel oil, bitumen, for processing into light motor fuel.
Benzene It is a colorless liquid with a characteristic odour. It is used for the synthesis of organic compounds, as a raw material for the production of plastics, as a solvent, for the production of explosives, in the aniline-dye industry.
Toluene is an analogue of benzene. It is used in the production of caprolactam, explosives, benzoic acid, saccharin, as a solvent, in the aniline-dye industry, etc.
Lubricating oils- Used in various fields of technology to reduce friction fur. parts, to protect metals from corrosion, as a cutting fluid.
Tar- black resinous mass. Used for lubrication, etc.
Petrolatum- a mixture of mineral oil and paraffins. They are used in electrical engineering, for lubricating bearings, for protecting metals from corrosion, etc.
Paraffin- a mixture of solid saturated hydrocarbons. Used as an electrical insulator, in chem. industry - to obtain higher acids and alcohols, etc.
Plastic– materials based on macromolecular compounds. Used for the production of various technical products and household items.
asphalt ore- a mixture of oxidized hydrocarbons. It is used for the manufacture of varnishes, in electrical engineering, for asphalting streets.
mountain wax- a mineral from the group of petroleum bitumens. It is used as an electrical insulator, for the preparation of various lubricants and ointments, etc.
artificial wax- purified mountain wax.
Coal - solid fossil fuel of plant origin, black or black-gray. Contains 75–97% carbon. Used as a fuel and as a raw material for the chemical industry.
Coke- a sintered solid product formed when certain coals are heated in coke ovens to 900–1050° C. Used in blast furnaces.
coke oven gas– gaseous products of coking of fossil coals. Comprises CH4, H2, CO and others, also contains non-combustible impurities. It is used as a high-calorie fuel.
ammonia water- liquid product of dry distillation of coal. It is used to obtain ammonium salts (nitrogen fertilizers), ammonia, etc.
Coal tar- a thick dark liquid with a characteristic odor, a product of the dry distillation of coal. It is used as a raw material for chemical industry.
Benzene- a colorless mobile liquid with a characteristic odor, one of the products of coal tar. They are used for the synthesis of organic compounds, as explosives, as a raw material for the production of plastics, as a dye, as a solvent, etc.
Naphthalene- a solid crystalline substance with a characteristic odor, one of the products of coal tar. Naphthalene derivatives are used to obtain dyes and explosives, etc.
Medications- the coke industry produces a number of drugs (carbolic acid, phenacytin, salicylic acid, saccharin, etc.).
Pitch- a solid (viscous) mass of black color, the residue from the distillation of coal tar. It is used as a waterproofing agent, for the production of fuel briquettes, etc.
Toluene- analogue of benzene, one of the products of coal tar. Used for the production of explosives, caprolactam, benzoic acid, saccharin, as a dye, etc.
Dyes- one of the products of coke production, obtained as a result of the processing of benzene, naphthalene and phenol. Used in the national economy.
Aniline- colorless oily liquid, poisonous. It is used to obtain various organic substances, aniline dyes, various azo dyes, the synthesis of drugs, etc.
Saccharin- solid white crystalline substance of sweet taste, obtained from toluene. It is used instead of sugar for diabetes, etc.
BB- derivatives of coal obtained in the process of dry distillation. They are used in the military industry, mining and other sectors of the national economy.
Phenol- a crystalline substance of white or pink color with a characteristic strong odor. It is used in the production of phenol-formaldehyde plastics, nylon synthetic fiber, dyes, medicines, etc.
Plastic– materials based on macromolecular compounds. Used for the production of various technical products and household items.
State budgetary educational institution of higher professional education
"Pyatigorsk State Pharmaceutical Academy"
Ministry of Health and Social Development of the Russian Federation
ORGANIC CHEMISTRY
SCHEMES AND DRAWINGS
Textbook for 2nd year students (3, 4 semesters)
(full-time education) for students of 2 and 3 courses (correspondence education)
in discipline C2.B.7 - "Organic Chemistry"
Pyatigorsk, 2011
UDC. 547(076)
Printed by decision of the CMS of the Pyatigorsk State Pharmaceutical Academy. Minutes No. 7 dated April 2, 2003
General edition: Head. Department, Professor Oganesyan E.T.
But on the basis of the current program in organic chemistry for pharmaceutical universities, a manual has been created that allows in a concise and accessible form to obtain information about the structure, methods of preparation and reactivity of the most important classes of organic compounds.
Reviewers: Professor Kompantsev V.A., Associate Professor Saushkina A.S.
Editorial Council:
Belikov V.G. (responsible editor) – prof. Ph.D.; Vergeichik E.N. (deputy editor) - prof., Ph.D.; Pogorelov V.I. (deputy editor) - prof., Ph.D.; Muravieva D.A. – Prof., Ph.D.; Gaevy M.D. – Prof., MD; Gatsan V.V. – Prof., Ph.D.
Karpova V.V.; Bratashova T.M. (responsible secretary)
1.1 Classification and main varieties of nomenclature
1.3 Substitutive nomenclature of functional derivatives
2.2 sp 3 -Hybridization. The structure of alkanes. Forecasting
2.3 Structure of cycloalkanes. reactionary forecasting
2.4 sp 2 -Hybridization. The structure of ethylene. Forecasting
2.5 The structure of butadiene-1,3. The concept of conjugation. Influence
2.7 sp hybridization. The structure of acetylene and the reaction
ability of alkynes .............................................................. ............................................... |
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Electronic structure of heterocyclic compounds. |
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Prediction of reactivity based on structure analysis .............................. |
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Features of the structure of the sp2 -hybrid nitrogen atom .............................................. |
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Electronic structure of pyridine ............................................................... .................... |
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Electronic structure of pyrrole ............................................................... ...................... |
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Electronic structure of pyrazole .............................................................. .................... |
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Isomerism of organic compounds ............................................................... ......................... |
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Types of isomerism .................................................. ................................................ |
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Properties of chiral compounds ............................................................... ................... |
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Rules for working with Fisher's projection formulas............................................... |
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Stereochemical nomenclature .................................................................. ............................... |
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D-, L-notation system .............................................. ................................. |
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R-,S-notation system .............................................. ................................. |
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Classification and mechanisms of organic reactions .............................................. |
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Classification of reactions .................................................................. ................................. |
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Mechanism of radical substitution reactions (SR) .............................................. |
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Mechanism of electrophilic substitution reactions (SE) .................................................. |
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The reaction mechanism of nucleophilic substitution (SN) at |
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sp3 -hybrid carbon atom .............................................. ................................. |
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Mechanism of electrophilic addition reactions (AdE ) .................................. |
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Mechanism of nucleophilic addition reactions (AdN) .............................................. |
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Reactivity and methods for obtaining organic substances in |
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diagrams ................................................. ................................................. ......................... |
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FOREWORD
The study of organic chemistry in pharmaceutical higher educational institutions sets as its most important goal the formation of a methodical approach for students to study the relationship between the structure of molecules and their properties.
The abundance of theoretical material creates the prerequisites for achieving this goal, however, students often experience an urgent need for such a source of information that would allow them to quickly and easily answer many questions related to the study of methods for obtaining and reactivity of organic compounds.
This study guide is precisely designed to help students in a concise and accessible form to obtain information,
concerning the structure and properties of the most important classes of organic compounds.
1. BASES OF CLASSIFICATION AND NOMENCLATURE OF ORGANIC COMPOUNDS
1.1 Classification and main varieties of the nomenclature of organic compounds
Organic chemistry is the chemistry of hydrocarbons and their derivatives. Several million organic compounds are now known. To study such a huge number of substances, they are divided into smaller groups - classes, within which the compounds have similarities in structure, and hence in chemical properties.
Organic substances can be classified according to various criteria: I - according to the structure of the carbon chain, they can be a) acyclic (carbon-
ice chains do not have cycles); b) cyclic (carbon chains are closed in cycles);
II - according to the nature of carbon-carbon bonds, substances are divided into a) limiting (in molecules there are only single carbon-carbon bonds); b) unsaturated (molecules have double or triple carbon-carbon bonds); c) aromatic (cyclic compounds with a special type of bond (see.
III - according to the presence of functional groups, the substances are assigned to different classes (the most important ones are presented in Table 1).
Nomenclature is a set of rules that allow you to give a name to each chemical compound. The replacement nomenclature is of the greatest importance; for derivatives of hydrocarbons, in addition to the substitutional one, the radical-functional nomenclature is often used. For some compounds, trivial (historically established) names are used.
1.2 Substitutive hydrocarbon nomenclature
Hydrocarbons are substances whose molecules consist only of carbon and hydrogen atoms.
To give a name to an acyclic hydrocarbon according to substitutional nomenclature, one must:
one . Select the parent structure using the following order:
1) the maximum number of multiple (double, triple) bonds;
2) maximum chain length;
3) the maximum number of substituents (radicals).
2* . Number the parent structure so that the smallest values (locants) get:
1) multiple bonds;
2) hydrocarbon substituents.
Each subsequent item is valid in the absence of the previous one, or if the previous one did not give an unambiguous answer.
3 . Name all radicals (see Table 2)
4. Compose a name according to the following scheme:
Console |
The ending |
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Hydrocarbon |
An - alkanes |
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deputies |
hydrocarbon |
En - alkenes |
indicating |
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alphabetically |
chain (ancestor- |
Yn - alkynes |
provisions |
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structure) |
Diene - alkadienes |
multiple bonds |
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For example: |
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3-ethylhexane |
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C2 H5 |
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3-methyl-3-ethylpentene-1 |
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CH3 2 |
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(CH2) |
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C3 H7 CH3 |
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3,3,4-trimethyl-4-propylnonin-1 |
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2-isopropylbutadiene-1,3 or 2-(1-methylethyl)butadiene-1,3 |
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Table 1 |
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table 2 |
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Names of some hydrocarbon substituents |
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Titles |
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trivial |
systematic |
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permissible |
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CH3- |
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(CH-) |
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isopropyl |
1-methylethyl |
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CH3-CH2-CH2-CH2- |
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CH CH2 |
isobutyl |
2-methylpropyl |
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sec-butyl |
1-methylpropyl |
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tert-butyl |
1,1-dimethylethyl |
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II Alkenyls |
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CH2- |
propen-2-yl |
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III alkynyls |
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not used |
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CH2 - |
not used |
propyn-2-yl |
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(C6 H5-) |
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2-methylphenyl |
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phenylmethyl |
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2-phenylethenyl |
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For cyclic hydrocarbons, either the cycle or the acyclic hydrocarbon chain associated with the cycle is chosen as the parent structure. The numbering of the cycle in the case of the presence of substituents is carried out from one substituent to another so that the locants receive the smallest value.
CH2-CH2-CH3 |
CH C2 H5 |
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sec-butylbenzene |
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1-methyl-2-propylcyclopentane |
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For some cyclic hydrocarbons, IUPAC rules allow the following trivial names:
CCH3 |
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ortho-xylene |
meta-xylene |
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para-xylene |
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naphthalene |
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anthracene |
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phenanthrene |
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H3 C C CH3 |
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1.3 Substitutive nomenclature for functional derivatives of hydrocarbons
Functional groups (F.G.) - groups of non-carbon atoms |
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nature, replacing hydrogen atoms in the hydrocarbon chain and |
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defining properties (function) of compounds. |
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The most important functional groups are: |
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Table 3 |
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Name |
Name |
Name |
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hydroxy- |
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SO3 H |
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carbonyl- |
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alkylthio- |
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carboxyl- |
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carbamoyl- |
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carbonyl- |
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According to the nature and quantity of PG, organic compounds are divided into the following |
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common groups: |
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Functional derivatives of hydrocarbons
Monofunctional |
Polyfunctional |
Heterofunctional |
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identical F.G.) |
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To give a name to the functional derivatives of hydrocarbons, it is necessary: 1. Choose the parent structure - a hydrocarbon chain linked:
1) with a functional group (for monofunctional compounds);
2) with a large number of functional groups (for polyfunctional compounds);
For new programs and textbooks, this issue becomes the most acute. Our school switched to the new textbooks by O.S. Gabrielyan and the new program, like most schools in the Zavolzhsky district, so we present the calendar-thematic planning for the course "Organic Chemistry" grade 10. Thematic planning is compiled according to the program developed by the Department of Educational Programs and ...
Activity. The search for methods and forms of teaching that contribute to the education of a creative personality has led to the emergence of some specific teaching methods, one of which is game methods. The implementation of gaming teaching methods in the study of chemistry in the conditions of compliance with didactic and psychological and pedagogical features, increases the level of training of students. The word "game" in Russian...
Secondly, a sufficient number of compounds are currently known that are insoluble in nonpolar solvents or, conversely, highly soluble in water, which, nevertheless, are classified as lipids. In modern organic chemistry, the definition of the term "lipids" is based on the biosynthetic relationship of these compounds - lipids include fatty acids and their derivatives. At the same time, in biochemistry...
The work is intended for teachers of chemistry, and may also be useful to students of pedagogical universities and colleges. 2.2. EXPLANATORY NOTE The need to develop an elective course for 10th grade students "Solving problems in organic chemistry of an increased level of complexity" is due to several reasons. In accordance with the basic curriculum of a complete secondary school for the study of chemistry in 2 ...
State budgetary educational institution of higher professional education
"Pyatigorsk State Pharmaceutical Academy"
Ministry of Health and Social Development of the Russian Federation
ORGANIC CHEMISTRY
SCHEMES AND DRAWINGS
Textbook for 2nd year students (3, 4 semesters)
(full-time education) for students of 2 and 3 courses (correspondence education)
in discipline C2.B.7 - "Organic Chemistry"
Pyatigorsk, 2011
UDC. 547(076)
Printed by decision of the CMS of the Pyatigorsk State Pharmaceutical Academy. Minutes No. 7 dated April 2, 2003
General edition: Head. Department, Professor Oganesyan E.T.
But on the basis of the current program in organic chemistry for pharmaceutical universities, a manual has been created that allows in a concise and accessible form to obtain information about the structure, methods of preparation and reactivity of the most important classes of organic compounds.
Reviewers: Professor Kompantsev V.A., Associate Professor Saushkina A.S.
Editorial Council:
Belikov V.G. (responsible editor) – prof. Ph.D.; Vergeichik E.N. (deputy editor) - prof., Ph.D.; Pogorelov V.I. (deputy editor) - prof., Ph.D.; Muravieva D.A. – Prof., Ph.D.; Gaevy M.D. – Prof., MD; Gatsan V.V. – Prof., Ph.D.
Karpova V.V.; Bratashova T.M. (responsible secretary)
1.1 Classification and main varieties of nomenclature
1.3 Substitutive nomenclature of functional derivatives
2.2 sp 3 -Hybridization. The structure of alkanes. Forecasting
2.3 Structure of cycloalkanes. reactionary forecasting
2.4 sp 2 -Hybridization. The structure of ethylene. Forecasting
2.5 The structure of butadiene-1,3. The concept of conjugation. Influence
2.7 sp hybridization. The structure of acetylene and the reaction
ability of alkynes .............................................................. ............................................... |
|||
Electronic structure of heterocyclic compounds. |
|||
Prediction of reactivity based on structure analysis .............................. |
|||
Features of the structure of the sp2 -hybrid nitrogen atom .............................................. |
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Electronic structure of pyridine ............................................................... .................... |
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Electronic structure of pyrrole ............................................................... ...................... |
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Electronic structure of pyrazole .............................................................. .................... |
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Isomerism of organic compounds ............................................................... ......................... |
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Types of isomerism .................................................. ................................................ |
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Properties of chiral compounds ............................................................... ................... |
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Rules for working with Fisher's projection formulas............................................... |
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Stereochemical nomenclature .................................................................. ............................... |
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D-, L-notation system .............................................. ................................. |
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R-,S-notation system .............................................. ................................. |
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Classification and mechanisms of organic reactions .............................................. |
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Classification of reactions .................................................................. ................................. |
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Mechanism of radical substitution reactions (SR) .............................................. |
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Mechanism of electrophilic substitution reactions (SE) .................................................. |
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The reaction mechanism of nucleophilic substitution (SN) at |
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sp3 -hybrid carbon atom .............................................. ................................. |
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Mechanism of electrophilic addition reactions (AdE ) .................................. |
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Mechanism of nucleophilic addition reactions (AdN) .............................................. |
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Reactivity and methods for obtaining organic substances in |
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diagrams ................................................. ................................................. ......................... |
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FOREWORD
The study of organic chemistry in pharmaceutical higher educational institutions sets as its most important goal the formation of a methodical approach for students to study the relationship between the structure of molecules and their properties.
The abundance of theoretical material creates the prerequisites for achieving this goal, however, students often experience an urgent need for such a source of information that would allow them to quickly and easily answer many questions related to the study of methods for obtaining and reactivity of organic compounds.
This study guide is precisely designed to help students in a concise and accessible form to obtain information,
concerning the structure and properties of the most important classes of organic compounds.
1. BASES OF CLASSIFICATION AND NOMENCLATURE OF ORGANIC COMPOUNDS
1.1 Classification and main varieties of the nomenclature of organic compounds
Organic chemistry is the chemistry of hydrocarbons and their derivatives. Several million organic compounds are now known. To study such a huge number of substances, they are divided into smaller groups - classes, within which the compounds have similarities in structure, and hence in chemical properties.
Organic substances can be classified according to various criteria: I - according to the structure of the carbon chain, they can be a) acyclic (carbon-
ice chains do not have cycles); b) cyclic (carbon chains are closed in cycles);
II - according to the nature of carbon-carbon bonds, substances are divided into a) limiting (in molecules there are only single carbon-carbon bonds); b) unsaturated (molecules have double or triple carbon-carbon bonds); c) aromatic (cyclic compounds with a special type of bond (see.
III - according to the presence of functional groups, the substances are assigned to different classes (the most important ones are presented in Table 1).
Nomenclature is a set of rules that allow you to give a name to each chemical compound. The replacement nomenclature is of the greatest importance; for derivatives of hydrocarbons, in addition to the substitutional one, the radical-functional nomenclature is often used. For some compounds, trivial (historically established) names are used.
1.2 Substitutive hydrocarbon nomenclature
Hydrocarbons are substances whose molecules consist only of carbon and hydrogen atoms.
To give a name to an acyclic hydrocarbon according to substitutional nomenclature, one must:
one . Select the parent structure using the following order:
1) the maximum number of multiple (double, triple) bonds;
2) maximum chain length;
3) the maximum number of substituents (radicals).
2* . Number the parent structure so that the smallest values (locants) get:
1) multiple bonds;
2) hydrocarbon substituents.
Each subsequent item is valid in the absence of the previous one, or if the previous one did not give an unambiguous answer.
3 . Name all radicals (see Table 2)
4. Compose a name according to the following scheme:
Console |
The ending |
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Hydrocarbon |
An - alkanes |
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deputies |
hydrocarbon |
En - alkenes |
indicating |
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alphabetically |
chain (ancestor- |
Yn - alkynes |
provisions |
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structure) |
Diene - alkadienes |
multiple bonds |
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For example: |
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3-ethylhexane |
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C2 H5 |
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3-methyl-3-ethylpentene-1 |
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CH3 2 |
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(CH2) |
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C3 H7 CH3 |
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3,3,4-trimethyl-4-propylnonin-1 |
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2-isopropylbutadiene-1,3 or 2-(1-methylethyl)butadiene-1,3 |
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Table 1 |
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table 2 |
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Names of some hydrocarbon substituents |
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Titles |
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trivial |
systematic |
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permissible |
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CH3- |
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(CH-) |
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isopropyl |
1-methylethyl |
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CH3-CH2-CH2-CH2- |
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CH CH2 |
isobutyl |
2-methylpropyl |
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sec-butyl |
1-methylpropyl |
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tert-butyl |
1,1-dimethylethyl |
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II Alkenyls |
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CH2- |
propen-2-yl |
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III alkynyls |
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not used |
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CH2 - |
not used |
propyn-2-yl |
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(C6 H5-) |
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2-methylphenyl |
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phenylmethyl |
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2-phenylethenyl |
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For cyclic hydrocarbons, either the cycle or the acyclic hydrocarbon chain associated with the cycle is chosen as the parent structure. The numbering of the cycle in the case of the presence of substituents is carried out from one substituent to another so that the locants receive the smallest value.
CH2-CH2-CH3 |
CH C2 H5 |
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sec-butylbenzene |
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1-methyl-2-propylcyclopentane |
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For some cyclic hydrocarbons, IUPAC rules allow the following trivial names:
CCH3 |
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ortho-xylene |
meta-xylene |
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para-xylene |
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naphthalene |
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anthracene |
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phenanthrene |
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H3 C C CH3 |
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1.3 Substitutive nomenclature for functional derivatives of hydrocarbons
Functional groups (F.G.) - groups of non-carbon atoms |
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nature, replacing hydrogen atoms in the hydrocarbon chain and |
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defining properties (function) of compounds. |
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The most important functional groups are: |
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Table 3 |
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Name |
Name |
Name |
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hydroxy- |
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SO3 H |
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carbonyl- |
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alkylthio- |
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carboxyl- |
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carbamoyl- |
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carbonyl- |
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According to the nature and quantity of PG, organic compounds are divided into the following |
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common groups: |
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Functional derivatives of hydrocarbons
Monofunctional |
Polyfunctional |
Heterofunctional |
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identical F.G.) |
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To give a name to the functional derivatives of hydrocarbons, it is necessary: 1. Choose the parent structure - a hydrocarbon chain linked:
1) with a functional group (for monofunctional compounds);
2) with a large number of functional groups (for polyfunctional compounds);
This manual contains in a visual form a course of organic chemistry, studied in grades 10-11 of a comprehensive school. The manual can be used when studying, summarizing and repeating educational material, and can also be useful in organizing systematic repetition in preparation for final or entrance exams.
Theory of radicals (30 years of the XIX century. J. Berzelius, J. Liebig, J. Dumas)
a) organic substances contain radicals;
b) radicals are always constant, do not undergo changes, pass from one molecule to another;
c) radicals can exist in free form.
The concept of "radical" is firmly established in chemistry. The theory was subsequently rejected.
Theory of types (40-50s of the 19th century. C. Gerard, A. Kekule and others)
a) all organic substances - derivatives of the simplest inorganic substances - such as hydrogen, water, ammonia, etc.
b) the formulas do not express the internal structure of the molecule, but the methods of formation, the properties determine all the atoms of the molecule.
c) it is impossible to know the structure of matter, each substance has as many formulas as there are transformations.
The theory made it possible to classify organic substances, to predict and discover some, with special attention to chemical transformations, but could not predict, indicate the ways of synthesis of new substances.
Content
I. Theory of the chemical structure of organic compounds
1 The emergence of organic chemistry as a science (1807 J. Berzelius) 3
2. Organic and inorganic substances. Composition and some properties of organic substances 4
3. Pre-structural theories 5
4. Connection between the concepts of the theory of chemical structure 6
5. Prerequisites for the emergence of the theory of the chemical structure of organic substances 7
6. Theory of chemical structure. Basic provisions (1,2) 8
7. Theory of chemical structure. Basic provisions (3.4) 9
8. Theory of chemical structure. Key points (5) 10
9. Algorithm for searching for possible isomers of alkanes (isomerism of the carbon skeleton) 11
10. Classification of chemical compounds typical of organic compounds (according to the type of chemical transformations) 12
11. Classification of chemical compounds typical of organic compounds (according to the type of bond breaking) 13
12. Classification of hydrocarbons 14
II. Limit hydrocarbons
1. Methane. physical properties. Molecule structure 15
2. Sp3 hybridization 16
3. Alkanes 17
4. Isomers and homologues 18
5. Alkanes (unbranched structure) and alkyls 19
6. Nomenclature (rational) 20
7. Nomenclature (systematic) 21
8. Determination of the qualitative composition of organic compounds 22
9. Chemical properties of alkanes 23
10. Obtaining alkanes 24
11. Use of alkanes 25
12. Cycloalkanes (cycloparaffins, naphthenes) 26
III. Unsaturated hydrocarbons
1. Ethylene (ethene). The structure of the molecule. sp2 hybridization 27
2. Alkenes (olefins, ethylene hydrocarbons) 28
3. Properties of alkenes 29
4. Properties of alkenes 30
5. Use of alkenes 31
6. Obtaining alkenes 32
7. Diene hydrocarbons (alkadienes) 33
8. Chemical properties of alkadienes (with conjugated bonds) Preparation 34
9. General characteristics of rubbers. Their structure and properties 35
10. Acetylene (ethyne). Molecule structure sp-hybritization 36
11. Comparison of the structure of the solecule of ethane, ethylene and acetylene. Comparison of o and ts connections 37
12. Alkynes (acetylenic hydrocarbons) 38
13. Chemical properties of alkynes 39
14. Chemical properties of alkynes 40
15. Application of acetylene 41
16. Obtaining acetylene and its homologues 42
IV. aromatic hydrocarbons
1. Benzene. physical properties. Formula Kekule 43
2. Electronic structure of benzene 44
3. Chemical properties of benzene 45
4. Chemical properties of benzene 46
5. Arenes (Aromatic hydrocarbons. Alkylbenzenes) 47
6. Toluene. Chemical properties. Mutual influence of atoms in a toluene molecule 48
7. Orientation rules in the benzene ring 49
8. The use of benzene. Getting arenas 50
9. Styrene. Naphthalene. Anthracene 51
10. Genetic relationship between groups of hydrocarbons 52
11. General information about hydrocarbon groups 53
12. General information about hydrocarbon groups 54
V. Alcohols and phenols
1. Limit monohydric alcohols 55
2. Chemical properties of alcohols 56
3. Ethanol (Ethyl alcohol) 57
4. Application of saturated monohydric alcohols 58
5. Methods for obtaining alcohols 59
6. Limit polyhydric alcohols 60
7. Ethers 61
8. Phenols 62
9. Chemical properties of phenol (by hydroxo group) 63
10. Chemical properties of phenol (on the benzene ring) 64
VI. Aldehydes and carboxylic acids
1. Aldehydes. Structure. Nomenclature. Isomerism 65
2. Formaldehyde. Receipt. Properties 66
3. Properties of aldehydes 67
4. Properties of aldehydes 60
5. Ketones G9
6. Preparation of aldehydes and ketones 70
7. Carboxylic acids. Homologous series 71
8. Some saturated monobasic acids 72
9. Carboxylic acids. Properties 73
10. Chemical properties of saturated monobasic carboxylic acids 74
11. Chemical properties of saturated monobasic carboxylic acids 15
12. Obtaining carboxylic acids 76
13.0 separate representatives of carboxylic acids. Classification 77
14. Separate representatives of carboxylic acids 78
VII. Complex ethers. Fats
1. Esters 79
2. Chemical properties of esters 80
3. Fats. Classification. Getting 81
4. Chemical properties of fats 82
5. Soaps 83
6. Synthetic detergents (CMC) 84
VIII. hydrocarbons
1. Carbohydrates. Compound. Classification 85
2. Glucose. Structure. Fructose 86
3. Glucose. Chemical properties 87
4. Glucose. Special properties. Application 88
5. Sucrose. Structure. Properties 89
6. Polysaccharides (CeH-mOsJn. Natural polymers 90
7. Starch and cellulose. Chemical properties 91
IX. Amines. Amino acids. Squirrels
1. Amines. Compound. Nomenclature. Isomerism 92
2. Amines. Chemical properties 93
3. Aniline. Structure. Properties 94
4. Amino acids. Nomenclature. Isomerism 95
5. Amino acids. Properties 96
6. Some amino acids of proteins 97
7. Obtaining and using amino acids 98
8. Proteins. Compound. Building 99
9. Protein structures 100
10. Chemical properties of proteins 101
11. Isomerism of classes of compounds 102
12. Genetic connection of organic substances 103
X Application
1. Qualitative reactions of organic compounds 104
2. Qualitative reactions of organic compounds 105
3. Periodic system of chemical elements 106
4. Symbols 107.
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