Classification of organic slabs for the budovaya carbonaceous skeleton. Classification of organic cases for functional groups

Classification of organic slabs for the budovaya carbonaceous skeleton. Classification of organic cases for functional groups

Organic semi-classifications are classified according to two main features: a coal-bearing skeleton and functional groups.

Behind the carbonaceous skeleton, acyclic, carbocyclic and heterocyclic layers are distinguished.

Acyclic spoluchy- To avenge vіdkritiy lansyug atomі ​​v ugleciu.

Carbocyclic layers– to avenge the closures of lances of carbon atoms and subdivide into alicyclic and aromatic ones. Before alicyclic all carbocyclic slabs, krіm aromatic ones can be seen. Aromatic half a cyclohexatriene fragment (benzene ring).

Heterocyclic slugs- sweep the cycles, which include the order of carbon atoms, one or more heteroatoms.

Due to the nature of functional groups, organic fields are subdivided into classy.

Table 2.1. The main classes of organic fields.

Functional group

Class z'ednan

Zagalna formula

Daily

in carbohydrates

Halogen

F, -Cl, -Br, -I (-Hal)

Halogen-pohidnі

R Hal

Hydroxyl

Alcohols and phenols

R-OH

Alkoxy

Forgive the Efiri

R-OR

Amino

NH2, >NH, >N-

Amenie

RNH 2 , R 2 NH, R 3 N

Nitro

Nitrospoluky

RNO 2

carbonyl

Aldehydes and ketones

Carboxylna

carboxylic acids

Alkoxycarbonyl

Folding air

Carboxamide

Amidi

carboxylic acids

Tiolna

Tioli

R-SH

Sulfo

sulfonic acids

R-SO 3 H

2. Nomenclature of organic crops.

At this hour, in organic chemistry, it’s hot systematic nomenclature, fragmented International Union of Pure and Applied Chemistry ( IUPAC). Behind her, they saved themselves and vikoristovuyutsya trivialі rational nomenclature.

Trivial nomenclature it is formed from historically formed names, which do not reflect the style of speech. The stench and vibra- tion of natural speech (lactic acid, sechovin, caffeine), characteristic dominance (glycerin, hydrophobic acid), mode of possession (pyruvic acid, sour ether), im pershovidkrivach (Michler's ketone, carbohydrate Chichibabin), the sphere of stagnation (ascor acid). The advantage of trivial names is their conciseness, which is allowed by the rules of IUPAC.

Systematic nomenclature є naukovoy and vіdobrazhaє warehouse, khіmіchnu and expanses of life. The name of the word is expressed behind the help of a collapsible word, the warehouses of which the songs of the elements and the molecules of speech reflect. At the heart of the IUPAC nomenclature rules are the principles replacement nomenclature, zgіdno z any molecule can be seen as similar to carbohydrates, in some atoms and water substitutions іnshі atoms аbо groups of atoms. When prompted to name a molecule, one sees such structural elements.

Pochatkov structure– head lance, carbonaceous lance, abo cyclic structure in carbot heterocycles.

carbohydrate radical- excess of the formula value in carbohydrates with free valences (div. table 2.2).

Characteristic group- functional group, tied to the parent structure or to enter to the її warehouse (div. table 2.3).

When folding, name the following rules sequentially.

    1. They assign the senior characteristic group and indicate the meaning of the suffix (div. table 2.3).
    2. To assign the parental structure behind such criteria as the fall of seniority: a) to avenge the senior characteristic group; b) revenge the maximum number of characteristic groups; c) revenge the maximum number of multiple links; d) maє maximum dozhina. The ancestral structure is indicated at the root of the name and in the beginning until the beginning of the lance and in the cycle: Z 1 - “met”, Z 2 - “et”, Z 3 - “prop”, Z 4 - “but”, Z 5 and dale - the root of the Greek numerals .
    3. They signify the rіven nasichennostі and vydbivayut їх at the suffix: “an” - no multiple links, “єн” - subvariant link, “ін” - triple link.
    4. Install other intercessors (carbohydrate radicals and young characteristic groups) and rearrange their names at the prefix in alphabetical order.
    5. Install prefixes to multiply - “di”, “three”, “tetra”, which indicate the number of the same structural elements (when the intercessors are redone in alphabetical order, do not shrug).
    6. Carry out the numbering of the parent structure so that the oldest characteristic group is the smallest ordinal number. Place locanti (numbers) before the name of the generic structure, before prefixes and before suffixes.


Table 2.2. Name the alkanes and alkyl radicals adopted by the IUPAC systematic nomenclature.

Alkan

name

Alkyl radical

name

CH 4

Methane

CH 3 -

Mityl

CH 3 CH 3

Yetan

CH 3 CH 2 -

Etil

Propane

CH 3 CH 2 CH 2 -

Propil

Isopropyl

CH 3 CH 2 CH 2 CH 3

n-butane

CH 3 CH 2 CH 2 CH 2 -

n- Butil

second- Butil

Pobutiy

Isobutyl

tert- Butil

CH 3 CH 2 CH 2 CH 2 CH 3

n-Pentane

CH 3 CH 2 CH 2 CH 2 CH 2 -

n- Pentil

isopentane

Isopentyl

Neopentane

neopentyl

Table 2.3. Name the characteristic groups (recovered in order of decreasing seniority).

Group

name

at the prefix

at the suffix

-(C)OOH*

ova acid

COOH

carboxy

carboxylic acid

SO 3 H

sulfo

sulfonic acid

-(C)HO

oxo

al

shaping

carbaldehyde

>(C)=O

oxo-

wine

VIN

hydroxyl

ol

mercapto

thiol

NH2

amino

amine

OR**

alkoxy, aroxy

F, -Cl, -Br, -I

fluorine, chlorine, bromine, iodine

NO 2

nitro

* The atom is charcoal, laying at the bow, entering to the warehouse of the cob structure.

** Alkoxy-groups and all the steps behind them are rearranged at the prefix behind the alphabet and do not care about the order of precedence.

Rational (radical-functional) nomenclatureі vykoristovuetsya for the names of simple mono- and bifunctional spoluk and deyakih classes of natural spoluk. The basis of the name is to become the name of a given class, either from one of the members of the homologous series of appointed intercessors. As a locant, as a rule, Greek letters are victorious.

    Classification of organic fields. functional group. General formulas of biologically important classes of organic compounds: alcohols, phenols, thiols, amines, ethers, sulfides, aldehydes, ketones, carboxylic acids

Organic sprouts classify on:

a) Budov of the coal lancer;

b) the presence of rich functional groups.

Functional groups- Tse defenders of a non-carbohydrate character, who signify the belonging of speech to the singing class and at once the same type of chemical power.

Classification of organic cases for functional groups:

organic speeches

Mono-, polyhomofunctional

heterofunctional

    Halogen-virgin

chloroethane

    Hydroxyacids

OH lactate

(hydroxypropanoic acid)

    aldehydes, ketones

    oxoacids

O pyruvate

(oxopropanoic acid)

    Alcohols, phenols, thiols

Entiol

3. Amino alcohols

ethanolamine

    carboxylic acids

H 3 C-COOH ethanoic acid

4. Amino acids

CH 3 alanine

(aminopropanoic acid)

    Forgive the Efiri

H 3 C-O-CH 3 methoxymethane

5. Carbohydrates

CH 2 - OH glucose

    Amenie

H 3 C-CH 2 -NH 2 ethylamine

    Folding air

H 3 C-C=O methyl ethanoate

Classification of organic speeches for budovoy radical:

organic speeches

acyclic

cyclical

carbocyclic

heterocyclic

cycloalkanes

boundary non-enforcement N parol

CH 4 - methane

C 2 H 6 - ethane

Sp 3 -hybridization

< 109 0 28׳

Sp 3 -hybridization

< 109 0 28׳

acetylene

sp hybridization

σ, 2π-star

Sp 2 -hybridization

σ, π-star

Sp 2 -hybridization

σ, π-star

Cirlopropane N

cyclohexane H CH 3 CH 3 imidazole

General formulas of biologically important classes of organic compounds: alcohols - R-OH

Phenols - OH

Thioli - R-SH

Amini - R-NH 2

simple efir - R 1 -O-R 2

sulfide - Me 2 Sx

aldehydes - R-COH

ketones - R 1 -C-R 2

carboxylic acids - R-COOH

    Electronic Budova atom vugletsyu. Types of hybridization of atomic orbitals. Covalent σ- and π-bonds, their main characteristics: strength, energy, polarity

In organic fields, coal can be found in one of three valence stations:

sp 3 -hybridization, In the event of a change of one s and three p-orbitals, with the exception of 4 hybridized orbitals, spreading in the open at a distance of 109 ° 28 'on one to one. The charcoal at such a station, having omitted the name of the tetragonal atom, the charcoal is sharpened at the boundary organic floors.

sp 2 -hybridization, In the event of a change of one s-two p-orbitals, 3 hybridized orbitals, spread in the same plane, under the apex of 120 ° in relation to one to one. The non-hybridized p-orbital is splayed perpendicular to the plane of the hybridized orbitals. The charcoal of such a steel is called trigonal, and the veins of the z'ednanny іz podvіynymi vyazkami.

sp-hybridization, If one of the s-orbital p-orbitals is mixed with the twins of 2 hybridized orbitals, splayed in space at a 180° angle (linearly), and two unhybridized p-orbitals are mutually spun together. This type of hybridization (sp-hybridization) is typical for charcoal, tied with a triangular ligature.

When a covalent bond is established in the molecules of organic semicolons, an electron pair populates molecular orbitals, which bind (MO), which generate lower energy. Fallow in the form of MO - σ-MO or π-MO - bonds, which are settled, are brought to σ- or p-type.

σ-Star– covalent linkage, solutions when the s-, p- and hybrid atomic orbitals (AT) are twisted on the axis, which rears the nuclei of the linking atoms (that is, with the axial twisting of the AT).

π-Star- covalent bond, which is to blame for the blocking of non-hybrid r-AT. Such an overlapping pose is straight, which hits the nuclei of atoms. π-bonds bind between atoms, already connected by σ-bonds (with which the subfolding and lossy covalent bonds are established). The π-link is weaker than the σ-link, through a smaller outward overlap of the p-AT.

The difference between σ- and π-molecular orbitals determines the characteristic features of σ- and π-links.

1. σ-links are similar to π-links. The reason for this is more efficient axial overlap of AT in the presence of σ-MO and the presence of σ-electrons between nuclei.

2. According to σ-bonds, intramolecular wrapping of atoms is possible, because the form of σ-MO allows such wrapping without breaking the link (with animated picture below)). Wrapping on the subvertical (σ + π) link is impossible without opening the π-link!

3. Electrons on π-MO, perebuvayushchie pose mezh'nuclear expanse, mayut more fluctuations in the line with σ-electrons. Therefore, the polarizability of the π-bond is significantly higher than that of the σ-bond.

Dovzhina zv'yazku- Stand between the nuclei of atoms, which you have done. With an increase in the part of s-AT in the hybrid orbital (with an increase in non-existence), the length of the link changes, more the s-orbital lies closer to the nucleus (may have a smaller radius), the lower p-orbital.

Energy zv'azku- The energy required for a homolytic bond to radicals or atoms.

Tab. 1. Actual characteristics of links

Molecule

Dovzhina, nm

Energy Е, kJ/mol

Steps of hybridization

592 (331 + 261)

813 (592 + 221)

Those that p-link is weaker than s-link, zamushuє dіti nevtіshnogo vysnovku, scho s nenaschennyh spolozheny may be characteristic, tobto. to go ahead of the reaction by multiple connections, because there is less energy and stench on them, moreover, more accessible from a spacious point of view.

The energy of the link is to lie in the nature of the element, the atoms of which make the link. So, the links of C-Hal add up the next series of mentality:

C-F > C-Cl > C-Br > C-І .

The value of the link in this row changes with the increase in the ordinal number of the element, but with the increase in the radius of the atom, the value of the link (with the increase in the electrostatic interchange changes).

In the corners of the coal with elements of the II period, the energy (energy) increases in the row: С-N< C-O < C-F , т.е. с увеличением электроотрицательности элемента, радиус которого при этом уменьшается (электростатическое взаимодействие усиливается).

Polarity

When a covalent bond is established between two identical atoms, the electron cloud is symmetrically spread between the nuclei of the atoms that bond, the bond is non-polar, and the molecule is non-polar (ethane, ethylene, acetylene).

As a covalent bond is established by different atoms with different electronegativity, the polar covalent bond is blamed, the electron shards are bound to the electronegative atom, and efficient partial charges are blamed on the atoms. Tsya polarity is constant (stationary), because it is mindful of internal officials, itself - by the nature of mutual atoms and the nature of the link between them.

Different electronegativity may be atoms of the very same element, as many atoms change at a different stage of hybridization. So, for vugletsyu:

In this way, the electronegativity of the atom increases with the increase in the part of the s-orbital in the hybrid orbital.

The appearance of a polar link in the molecule zooms in on the polarity of the entire molecule, but it adds power to the speech. So, polar speeches, on the basis of non-polar ones, are more often distinguished in polar rhetoricians, they sound more like boiling and melting temperatures, it is easier to react to ionic mechanisms.

    Pojdnannya, see success: π, π- iR , π-conjugation. The following systems have been obtained with lancet acid: 1,3-diene (butadiene, isoprene, alyl carbocation); polyene (carotenoids, vitamin A); heteroconjugated systems (α, β-unsaturated carbonyl subgroups, carboxyl group)

Got system blame when joining to sp 2 -hybridized carbon atom in the molecule of the intercessor, scho to avenge in your warehouse the dependent link (π, π-conjugation) or may p-orbital (p, π-conjugation). When it comes to the right electrons, the π-electron gap is distributed along all π-orbital systems, and not between two terrestrial p-orbitals. In the case of p, π-conjugation, the electron gap dilocalizes between the orbitals of the π-bond and the p-orbital of the heteroatom - Pro, N, S and in, which carry an unmatched pair of electrons, electron mismatches or not. The day is an energetically viable process, because as a result of electron dilization, energy is seen, and the molecule becomes thermodynamically more stable. The level of thermodynamic stability is estimated as a difference in the energy of molecules from the obtained and insulating bonds - the energy of obtaining (the energy of delocalization).

Organic parts are most often classified according to two criteria - the carbonaceous skeleton of the molecule, or the presence in the molecule of the organic part of the functional group.

The classification of organic molecules behind the carbonaceous skeleton can be seen from the following scheme:

Acyclic slabs - all slabs from an open carbon lance. Їx basis to form aliphatic half-words (type of walnut aleiphatos oliya, fat, resin ) – in carbohydrates and їх хідні, carbonic atoms and some of them are related to each other in the form of non-decomposition or degeneration of the lance.

Cyclic spoluki - tse spoluki, scho avenge the closures of the lancers. Carbocyclic halfs in the warehouse of the cycle should be replaced only by atoms of carbon, heterocyclic in the warehouse of the cycle, crim atoms in carbon, revenge one or more of heteroatoms (atoms N, O, S and in.).

Fallow, according to the nature of the functional groups similar to carbohydrates, can be divided into classes of organic soils. Functional group– either an atom or a group of atoms, as a rule, of a non-carbohydrate character, which determines the type of chemical power of the semin and її belonging to the first class of organic spoluk. As a functional group, in non-existent molecules, there are dependent or lossy links.

The name of the functional group

Name the class Z'ednan

Zagalna formula class

Carboxyl-COOH

carboxylic acids

Sulfonic-SO 3 H

sulfonic acids

Oxo group (carbonyl)

Aldehyde

Oxo group (carbonyl)

Hydroxyl -OH

Tiolna (mercapto)-SH

Thioli (mercaptan)

F, -Cl, -Br, -I

Halogen-pohidnі

Alkoxy - OR

Forgive the Efiri

Alkilthiolna-SR

Tioefiri

Nitrospoluky

Alkoxycarbonyl

Folding air

Amino-NH 2

RNH 2 ,R 1 NHR 2, R 1 R 2 R 3 N

Carboxamide

2.2 Principles of chemical nomenclature - systematic nomenclature iupak. Replacement of that radical-functional nomenclature

The nomenclature is a system of rules that allows you to give an unambiguous name to the object. At the core replacement nomenclature lie vibir parental structure. The name will be like a collapsible word that is formed from the root (the name of the generic structure), suffixes, which reflect the steps of non-existence, prefixes and endings, which indicate the character, number and position of intercessors.

The ancestral structure (generic hydride) is priceless acyclic or cyclical, in the structure, which is up to carbon atoms or other elements, only atom and water are added.

Protector - ce functional (characteristic) group chi in carbohydrate radical, binding from the parent structure.

A characteristic group is a functional group, tied to the parental structure, or often to enter the її warehouse.

Head group- a characteristic group that should be introduced when forming names at the end of the name when the names are approved for additional functional groups.

Intercessors, connected with the ancestral structure, are divided into two types. Protectors of the 1st type- carbohydrate radicals and non-carbohydrate characteristic groups, which appear in the name only in prefixes.

Intercessors of the 2nd type- characteristic groups, which are indicated in the name of the fallow in the seniority or at the prefix, or at the end. At the guidance below the tables, the seniority of intercessors changes to the beast to the bottom.

Functional group

Completion

carboxylic acid

carboxy

carboxylic acid

ova acid

Sulfonic acids

sulfonic acid

carbonitrile

Aldehyde

carbaldehyde

Hydroxy

Mercapto

*- An atom in the coal of the functional group enters the warehouse of the parent structure.

The ordering of the name of the organic organization is carried out at the singing sequence.

    Designate a characteristic characteristic group, for example, won't. The head group is introduced at the end of the name of the task.

    Designate the cob structure of the half-shell. As a parental structure, as a rule, the cycle in carbocyclic and heterocyclic layers, or the head carbonaceous lance in acyclic layers, is taken. Golovne vugletsevy kolo to choose from the improvement of the advancing criteria: 1) the maximum number of characteristic groups of the 2nd type, which are indicated both by prefixes and suffixes; 2) the maximum number of multiple links; 3) the maximum length of the lanceg; 4) the maximum number of characteristic groups of the 1st type, which are indicated only by prefixes. The next criterion is victorious, just as the previous criterion does not lead to an unambiguous choice of the parental structure.

    Carry out the numbering of the parent structure in such a way that the smallest number was taken by the oldest characteristic group. For the obviousness of dekіlkoh of the same senior functional groups, number the parent structure in such a rank that the intercessors would take away the smallest numbers.

    Name the parental structure, in the name of which the oldest is characteristic of the group to end. Presence and non-existence of the generic structure is indicated by suffixes - an,-en,-in, what to say before the end, like giving the older characteristic group

    They give names to the intercessors, as the names of the z'dnanny appear at the sight of the prefixes, and they are rearranged in a single alphabetical order. Numerical prefixes in a single alphabetical order are not reversed. The position of the skin protector and the skin multiple link must be indicated by numbers, which correspond to the number of the carbon atom, for which the protector is indicated (for a multiple link, indicate the smaller number of the carbon atom). Put numbers before prefixes and then after suffixes or endings. The number of intercessors of the same intercessors are shown in the name for the help of multiplying prefixes di, three, tetra, penta ta and etc.

The name of the task is formed after the scheme:

Attach the name for the replacement IUPAC nomenclature:

Radical-functional nomenclature maє obmezhene vikoristannya. The head rank won out with the names of simple mono- and bifunctional sections.

If there is one functional group in the molecule, then the name of the half is formed from the name of the carbohydrate radical and that characteristic group:

In different folded folds, choose the parent structure, which can be called a trivial one. Roztashuvannya intercessors, who are indicated in prefixes, are carried out for the help of numbers, walnut letters or prefixes ortho-, meta-, para-.

2.3 Conformations

Z'ednannya, which may have the same yakіsny and kolkіsny warehouse, the same chemical budovu, but still roztashuvannyam in the expanse of atoms and groups of atoms, are called stereoisomers. Conformation - all the space for the separation of atoms in a molecule, afterward wrapping atoms and groups of atoms into about one and a few ordinary bonds. Stereoisomers that are converted one on one as a result of wrapping around a simple link are called conformational isomers. For this image on a flat surface, stereochemical formulas or Newman projection formulas are most often used.

In stereochemical formulas, the link, which lies near the square of the paper, is depicted with a little rice; links, straightened to posterigach, denoted by a bold wedge; zv'azki, roztashovanі behind the flat (like in vіd poserigach), signify shading wedge. Stereochemical formulas of methane and ethane can be presented in the following order:

To remove Newman's projection formulas in the molecule, select the C-C links, the carbon atom that is far from the posterigach is designated as a column, the carbon atom closest to the posterigach and the C-C bonds is indicated by a dot. Three more links of atoms in the coal on the surface are seen at a depth of 120, one at a time. Stereochemical formulas for ethane can be applied to Newman's projection formulas in the following order:

The wrapping of ordinary links in a molecule of methane does not lead to a change in the spacious position of atoms in a molecule. Ale in the etane molecule, afterward, the wrapping around the ordinary C-C bond changes the distribution of atoms, tobto. blame conformational isomers. For the minimum cut to turn (torsion cut), it is accepted to take a cut of 60. For ethane, two conformations are blamed in such a rank, which go one into one at the last turns by 60. Qi conformations differ in energy. Conformation, among the yakіy atoms (protectors) change at the nearest camp, the shards of the link obscure one alone, are called obscured. Conformation, in which atoms (protectors) are as far as possible one in one, are called galvanized (anti-Conformation). For ethane, the energy difference in conformations is small and equal to 11.7 kJ/mol, which can be compared with the energy of thermal rux of ethane molecules. Such a small difference in the energies of the conformational isomers of ethane does not allow them to be seen and identified at normal temperatures. More high energy can obscure the conformation torsion stresses (Pitzer stresses) - vzaєmodіy, vyklikanyh vіdshtovhuvannyam opposing zv'yazkіv. In galvanized conformations, the bond is maximally distant and the interplay between them is minimal, which confuses the minimal energy of the conformation.

In butane, when turning around, the bond between other and third carbon atoms wins out dodatkovo bevelled conformation ( gosh-Conformation). Cream of tsgogo, obscured by the conformations of butane, energizes.

The tulle (vih_dna) conformation of butane is characterized by maximum energy, which is indicated by the presence torsionі van der Waals voltage. Van der Waals stresses in this conformation are due to the mutual inclusion of volumes (equal to the H atom) of methyl groups, which appeared to be close. Such an interplay increases the energy of conformation, the roblyachs are energetically invisible. When rotated by 60 vinica bevelled conformation, in a small amount of torsional tension (links do not cover one another), and van der Waals tensions actually change for the radii in the distance between the methyl groups one and one, the energy of the gosh-conformation is less by 22 kJ / mol of the energy of the conformation obscured. With a 60 turn, the bend is obscured by the conformation; in yak, prote, the place has less torsion stress. Between the H atom and the CH 3 group, van der Waals forces are not blamed for the insignificant size of the H atom. Make a 60 chergovy turn to a tangled conformation, in which there are no torsional and van der Waals stresses, the shards of the link do not cover one one, but the volume of the methyl groups is maximally one in one. The energy of the halved conformation is minimal, less than the energy of the folded conformation by 25.5 kJ/mol, and equal to the energy of the skewed conformation is less by 3.5 kJ/mol. Advance turns to induce at vinic eclipsed, beveled and outward eclipsed conformations. For the greatest minds, the majority of butane molecules are overwhelmed by looking like sumish goshta anti-conformers.

All organic slabs fallow due to the nature of the carbonaceous skeleton can be subdivided into acyclic and cyclic.

Acyclic (non-cyclic, lanciugov) half-baked are also called bold or alіphatic. Name the reasons for this, that one of the first good cases of this type were natural fats. Among the acyclic columns, the borders are distinguished, for example:

and non-existent, for example:

In the midst of cyclical half-times, you can see carbo-cyclic, molecules of which there are rings of carbon atoms, heterocyclic kіltsya kakіh mіstya kіm vugleciu atoms іnshih elementіv (sour, sіrki, nitrogen and іn).

Carbocyclic semiions are subdivided into alicyclic (boundary and non-saturated), similar in terms of power to aliphatic and aromatic, thus avenging benzene rings.

You can look at the classification of organic fields by looking at a short scheme

Before the storehouse of rich organic spoluk krіm vuglec i vdnyu enter іnshі elementi, moreover, in apparently functional groups - groups of atoms, which signify the chemical power of this class of spoluk. The presence of these groups allows for the extension of the designation of more typical organic sprouts to the class and ease of their development. Acts of the most characteristic functional groups and the most important class with reference to the table

functional
group

name
groupie
Klasi
day

-OH

Hydroxide

carbonyl

alcohol

C2H5OH

Ethyl alcohol

Aldehyde

ostovy aldehyde

ketoni

Carboxyl

carbonic
acids

octoic acid

-NO 2 Nitrogroup Nitrospoluky

CH 3 NO 2

Nitrometpn

-NH2


Lecture №1

CLASSIFICATION, NOMENCLATURE and Isomeriya of ORGANIC STUDIES

1. Classification of organic soils.

2. Nomenclature of organic crops.

3. Structural isomerism.

1. Classification of organic soils.

Organic semi-classifications are classified according to two main features: a coal-bearing skeleton and functional groups.

Behind the carbonaceous skeleton, acyclic, carbocyclic and heterocyclic layers are distinguished.

Acyclic spoluchy- To avenge vіdkritiy lansyug atomі ​​v ugleciu.

Carbocyclic layers– to avenge the closures of lances of carbon atoms and subdivide into alicyclic and aromatic ones. Before alicyclic all carbocyclic slabs, krіm aromatic ones can be seen. Aromatic half a cyclohexatriene fragment (benzene ring).

Heterocyclic slugs- sweep the cycles, which include the order of carbon atoms, one or more heteroatoms.

Due to the nature of functional groups, organic fields are subdivided into classy.

Table 1. Main classes of organic crops.

Functional group

Class z'ednan

Zagalna formula

Daily

in carbohydrates

F, -Cl, -Br, -I (-Hal)

Halogen-pohidnі

Hydroxyl

Alcohols and phenols

Alkoxy

Forgive the Efiri

NH2, >NH, >N-

Nitrospoluky

carbonyl

>c=o<="" center="">

>c=o>

Aldehydes and ketones

Carboxylna

carboxylic acids

Alkoxycarbonyl

Folding air

Carboxamide

carboxylic acids

Tiolna

sulfonic acids

2. Nomenclature of organic crops.


At this hour, in organic chemistry, it’s hot systematic nomenclature, broken up by the International Union of Pure and Applied Chemistry ( IUPAC). Behind her, they saved themselves and vikoristovuyutsya trivialі rational nomenclature.

Trivial nomenclature it is formed from historically formed names, which do not reflect the style of speech. The stench and vibra- tion of natural speech (lactic acid, sechovin, caffeine), characteristic dominance (glycerin, hydrophobic acid), mode of possession (pyruvic acid, sour ether), im pershovidkrivach (Michler's ketone, carbohydrate Chichibabin), the sphere of stagnation (ascor acid). The advantage of trivial names is their conciseness, which is allowed by the rules of IUPAC.

Systematic nomenclature є naukovoy and vіdobrazhaє warehouse, khіmіchnu and expanses of life. The name of the word is expressed behind the help of a collapsible word, the warehouses of which the songs of the elements and the molecules of speech reflect. At the heart of the IUPAC nomenclature rules are the principles replacement nomenclature, zgіdno z any molecule can be seen as similar to carbohydrates, in some atoms and water substitutions іnshі atoms аbо groups of atoms. When prompted to name a molecule, one sees such structural elements.

Pochatkov structure– head lance, carbonaceous lance, abo cyclic structure in carbot heterocycles.

carbohydrate radical- excess of the formula value in carbohydrates with free valences (div. table 2).

Characteristic group- functional group, tied to the parent structure or to enter to the її warehouse (div. table 3).

When folding, name the following rules sequentially.

1. Designate the senior characteristic group and indicate the significance of the suffix (Div. Table 3).

2. Appoint the parent structure behind such criteria as a fall in seniority: a) avenge the senior characteristic group; b) revenge the maximum number of characteristic groups; c) revenge the maximum number of multiple links; d) maє maximum dozhina. Pochatkovu structure is assigned to the root of the name in the beginning to the beginning of the lansy or to the cycle: C1 - "met", C2 - "et", C3 - "prop", C4 - "but", C5 and dale - the root of the Greek numbers.

3. Designate the degree of presence and add them to the suffix: “an” - no multiple links, “єн” - subway link, “ін” - triple link.

4. Install other defenders (carbohydrate radicals and young characteristic groups) and rearrange their names at the prefix in alphabetical order.

5. Install prefixes to multiply - “dі”, “three”, “tetra”, which indicate the number of the same structural elements (when the intercessors are redeemed in alphabetical order, do not vacate).

6. Carry out the numbering of the parent structure so that the oldest characteristic group is the smallest ordinal number. Place locanti (numbers) before the name of the generic structure, before prefixes and before suffixes.


Table 2. Names of alkanes and alkyl radicals adopted by IUPAC systematic nomenclature.

name

Alkyl radical

name

Isopropyl

n-butane

n-Butyl

sec-Butyl

Pobutiy

Isobutyl

tert-Butyl

CH3CH2CH2CH2CH3

n-Pentane

CH3CH2CH2CH2CH2-

n-Pentyl

isopentane

Isopentyl

Neopentane

neopentyl

Table 3

*Atom in the corner, laying at the shackle, enter to the warehouse of the cob structure.

**Alkoxy-groups and all steps behind them are ranked at the prefix after the alphabet and do not care about the order of precedence.

Rational (radical-functional) nomenclature vykoristovuetsya for the names of simple mono- and bifunctional spoluk and deyakih classes of natural spoluk. The basis of the name is to become the name of a given class, either from one of the members of the homologous series of appointed intercessors. As a locant, as a rule, Greek letters are victorious.

3. Structural isomerism.

Izomiri- the chains, which may have the same warehouse and molecular weight, but different physical and chemical power. The power of authority is measured by the power of the minds of their chemical and spacious life.

Pid chemical everyday understand the nature of that sequence of links between atoms in a molecule. Isomers, the molecules of which are considered for chemical budovaya, called structural isomers.

Structural isomers may vary:

      behind the coal skeleton

      by the position of multiple links and functional groups

      by type of functional groups

1. Isomerism

The concept of "isomer" was introduced by Berzelius in 1830. Vіn vyznav "izomery" like speech, scho mayut the same warehouse (molecular formula), but different power. The statement about the isomer Berzelius centuries after having established that cyanic acid HOCN is identical to the depot of tinnitus or isocyanic acid O=C=NH.

There are two main types of isomer: structuralі space(stereoisomerism).

Structural isomers are connected one by one in the order of links between atoms in a molecule; stereoisomers - the separation of atoms in space with the same order of connections between them.

2. Structural isomerism

Structural isomerism is subdivided into sprat varieties.

Isomerism of the carbonaceous skeleton bound by a different order of bonding between carbon atoms, which make up the skeleton of the molecule. So, you can use only one non-cyclic number of carbohydrates from trio with C atoms - propane (I). In carbohydrates of the same type with chotirma atoms, there can already be two: n-butane (II) and isobutane (III), and with five C atoms - three: n-pentane (IV), isopentane (V) and neopentane (VI): ammonia, but 1,3-dinitrobenzene (XI) does not react with NH3.

A number of aliphatic simple ethers, sulfides and amines have a special type of isomer. metamerism, is bound to different positions of the heteroatom in the carbonaceous lance with Metamers є, for example, methylpropyl (XII) and diethylovium (XIII) ethers:

Isomeriya non-existent spoluche can be buti viclikana different positions of a multiple bond, like, for example, in butene-1 (XIV) and butene-2 ​​(XV), in vinilucic (XVI) and crotonic (XVII) acids:

Most of the differences in structural isomers have signs of skeletal isomerism and positional isomerism, even if different functional groups lie down to different classes of speeches, after which the stench is considered one of the same is significantly larger, the lower of the same type is considered. For example, isomers are propylene (XVIII) and cyclopropane (XIX), ethylene oxide (XX) and acetaldehyde (XXI), acetone (XXII) and propionic aldehyde (XXIII), dimethyl ether (XXIV) and ethyl alcohol (XXV), allene ( XXVI) and methylacetylene (XXVII):

Let us distinguish the type of structural isomer є tautomerism(Equally important dynamic isomeria) - the basis of speech in two or more isomeric forms, which is easy to move one into one. Thus, acetoacetic ether has an equally important sum of ketone (XXVIII) and enol (XXIX) forms:

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