Functional derivatives of carbonic acid. Amides of carbonic acid and their derivatives Derivatives of carbonic acid

Carbonic acid, like many other acids, forms a number of derivatives: salts, esters, chlorine anhydrides, amides, etc.

For medicine, amides of carbonic acid are of great interest, since their derivatives are valuable drugs.

Carbonic acid, as a dibasic acid, forms two types of amides: a) an incomplete amide (a product of the replacement of one hydroxyl by an amino group) - carbamic acid; b) complete

amide (a product of substitution of two hydroxyls for amino groups) - urea, or urea.

Carbamic acid in the free state is unknown due to its high tendency to decompose into carbon dioxide and ammonia. But its acid chlorides, co-li, esters are well known. For medical practice, carbamic acid esters, called urethanes, which have a hypnotic effect, are important.

Depending on the nature of the alcohol with which carbamic acid is esterified, various urethanes can be obtained.

Of the urea derivatives, of greatest interest to medicine are its acyl derivatives, in which the hydrogen of the amino group of urea is replaced by an acid residue - acyl (Ac is the residue of any acid).

Atsilyshe urea derivatives were first obtained by N. N. Zinin and named by him ureides.

When urea reacts with a monobasic carboxylic acid, open (acyclic) ureides are formed.

In the interaction of urea with a dibasic carboxylic acid, both open and closed (cyclic) ureides can be obtained, depending on the reaction conditions.

When the hydrogens in the methylene group (position 5) of the barbituric acid molecule are replaced by various radicals, many of its derivatives (barbiturates) can be obtained, which are used in medicine as hypnotic drugs.

By physical properties, drugs related to ureides and urethanes are white crystalline solids, hardly soluble in water, with the exception of salts.

The chemical properties of ureides and urethanes have a number of common features - when heated with alkali, both release ammonia and sodium carbonate, and when acidified, sodium carbonate releases gas bubbles (CO2).

Other reaction products during the interaction of urethanes and ureides with alkali make it possible to distinguish them from each other.

In the case of urethanes, alcohol (I) is formed, in the case of ureides, the sodium salt of the corresponding acid (II) is formed.

One of the representatives of urethanes is the drug meprotan, of the open ureides, bromisoval finds application in medicine.

Description. Solubility. Odorless white crystalline powder, saline-alkaline taste, soluble in water, practically insoluble in alcohol. Aqueous solutions have a slightly alkaline reaction. When shaking and heating up to 70 ° C aqueous solutions of NaHCO 3, a double salt of Na 2 CO 3 is formed · NaHC03.

Receipt

Sodium bicarbonate was discovered in 1801 by the scientist V. Rose. The preparation is obtained by saturating purified soda ash with carbon dioxide:

Na2CO3 · 10 H 2 O + CO 2 → 2NaHCO 3 + 9 H 2 O

drinking calcined dioxide

Authenticity

With a qualitative analysis, pharmacopoeial reactions are carried out for the Na + ion and HCO 3 - - and he.

General reactions to CO 3 2- and HCO 3 - - ions:

Under the action of a strong mineral acid, a rapid release of CO 2 is observed:

NaHCO 3 + HCl → NaCl + H 2 O + CO 2

CO 2 + Ca(OH) 2 → CaCO 3 ↓ + H 2 O

white lime dioxide

carbon water

Distinctive reactions:

1) Carbonates can be distinguished from hydrocarbons by the color of the indicator - phenolphthalein. When sodium carbonate is dissolved in water, the reaction of the medium is slightly alkaline and therefore the color of the indicator is pink: Na 2 CO 3 + H 2 O → NaHCO 3 + NaOH

When dissolving sodium bicarbonate, the reaction of the medium is acidic, and the indicator is colorless or slightly pink: NaHCO 3 + H 2 O → H 2 CO 3 + NaOH

H 2 CO 3 → CO 2 + H 2 O

2) With a saturated solution of magnesium sulfate, carbonates form a white precipitate at room temperature, and hydrocarbons - only when boiled:

4 Na 2 CO 3 + 4 MgSO 4 + 4 H 2 O → 3 MgCO 3 Mg(OH) 2 3 H 2 O↓ + 4 Na 2 SO 4 + CO 2

2 NaHCO 3 → Na 2 CO 3 + CO 2 + H 2 O

Goodness

NaHC03: 1) allowed: Cl -, K +, Ca 2+, Fe, As.

The specific admixture of CO 3 2– is determined by calcination at a temperature of 300 ° C. The loss in mass must be at least 36.6%. The more impurities of carbonates, the less the loss in mass on ignition. The theoretical loss is 36.9%. The difference between the theoretical weight loss and that indicated in the GF determines the allowable limit of carbonate impurities in the preparation - 0.3%.

2) not allowed: NH 4 + salts and heavy metals.

quantitation

Acidimetry, direct titration, the sample is dissolved in freshly boiled and cooled water to remove CO 2, titrated with 0.5 N HCl, methyl orange indicator. E = M.

Application. Storage.

store in a well sealed container. The substance is stable in dry air, but slowly loses CO 2 in humid air and forms Na 2 CO 3 .

Apply as an antacid inside, as well as externally in the form of rinses, rinses, inhalations of 0.5 - 2% solutions.

Features of the preparation of NaHCO 3 injection solutions

NaHCO 3 injection solutions are sterilized at 100°C for 30 minutes. In this case, CO 2 is formed, therefore, bottles with an injection solution of NaHCO 3 are filled to 2/3 of the volume at a temperature of not more than 20 o C.

After sterilization, the solution is cooled until complete dissolution of the resulting CO 2 .

Description. Solubility. Colorless transparent crystals or white crystalline powder, odorless, slightly bitter taste. It rises and vanishes. Slightly soluble in water, soluble in alcohol, slightly soluble in chloroform, ether, turpentine.

Receipt

Terpinhydrate obtained from pinene - a product of fractional distillation of turpentine. Pinene is hydrated under the action of sulfuric acid in the cold for 10 days. Then the mixture is neutralized with soda, the terpinhydrate is separated, purified and recrystallized.

Authenticity

General reactions

Drugs identify alcohol hydroxyl:

1) ester formation reaction with acids. This property is used when obtaining validol. Esterification of menthol and terpinhydrate with acetic anhydride gives acyl derivatives in the form of a white precipitate; its melting point can be determined.

2) oxidation reaction. Menthol is oxidized by weak oxidants to ketone-menthone. Under the action of strong oxidizing agents, menthol decomposes to formic, acetic, butyric and oxalic acids.

Specific reactions

Terpinhydrate when interacting with an alcoholic solution of ferric chloride during evaporation, it forms carmine-red, violet and green coloring in different places of the evaporation dish. When benzene is added to the oxidation products, a blue color is formed.

Terpinhydrate is also opened by a dehydration reaction in the presence of concentrated sulfuric acid to form turbidity and aromatic odor:

Goodness

Terpinhydrate. 1) Allow:

sulfate ash and heavy metals.

Carbon dioxide (carbon dioxide)-participant in many carboxylation and decarboxylation reactions in vivo And in vitro.

Carboxylation is possible when compounds with a partial negative charge on the carbon atom react with carbon dioxide. In the body, the interaction of carbon dioxide with acetyl coenzyme A leads to the formation of malonyl coenzyme A.

Like carbonic acid itself, some of its derivatives are also unknown in free form: ClCOOH monochloride and monoamide - carbamic acid H 2 NCOOH. However, their esters are quite stable compounds.

For the synthesis of carbonic acid derivatives, one can use phosgene(dichloranhydride) COCl 2, easily formed by the interaction of carbon monoxide with chlorine in the light. Phosgene is an extremely poisonous gas (bp. 8 o C), in the First World War it was used as a chemical warfare agent.

Ethyl ester of chloroformic acid, when reacted with ammonia, forms ethyl ester of carbamic acid H 2 NCOOC 2 H 5 . Esters of carbamic acid (carbamates) have a common name - urethanes.

Urethanes have found application in medicine as medicines, in particular meprotan And ethacizin.

Urea (urea)(NH 2) 2 C=O is the most important nitrogen-containing end product of human metabolism (about 20-30 g/day of urea is excreted in the urine).

Acids and alkalis, when heated, cause the hydrolysis of urea; in the body, it is hydrolyzed by the action of enzymes.

When slowly heated to a temperature of 150-160 ° C, urea decomposes with the release of ammonia and the formation biuret.

When biuret interacts in alkaline solutions with copper(II) ions, a characteristic violet color is observed due to the formation of a chelate complex (biuret reaction). The biuret residue in the chelate complex has an imide structure.

Derivatives of carboxylic acids containing a urea residue as a substituent are ureides. They are used in medicine, in particular α-bromoisovaleric acid ureide - bromized
(bromural) - used as a mild sleeping pill. Its effect is due to a combination of bromine and isovaleric acid residue known for its inhibitory effect on the central nervous system.

Guanidine (iminourea)- a nitrogenous derivative of urea - is a strong base, since the conjugate acid - guanidinium ion - is mesomerically stabilized.

The guanidine residue is part of the α-amino acid - arginine and the nucleic base - guanine.

3.2 Heterofunctional compounds in life processes

general characteristics

Most substances involved in metabolism are heterofunctional compounds.

Compounds are called heterofunctional, in the molecules of which there are different functional groups.

Combinations of functional groups characteristic of biologically important compounds are presented in Table 3.2.

Table 3.1. The most common combinations of functional groups in biologically important aliphatic compounds

Among the heterofunctional compounds in natural objects, the most common are amino alcohols, amino acids, hydroxycarbonyl compounds, as well as hydroxy and oxo acids (Table 9.2).

Table 9.2. Some hydroxy and oxo acids and their derivatives

* For di- and tricarboxylic acids - with the participation of all carboxyl groups. For incomplete salts and functional derivatives, a prefix is ​​added hydro)-, e.g. "hydroxalate" for the anion HOOC-COO - .

Of particular biological importance α-amino acids are covered in chapter 12. Polyhydroxy aldehydes and polyhydroxy ketones (carbohydrates) are covered in chapter 13.

In the aromatic series, important natural biologically active compounds and synthetic drugs (see 9.3) are based on i-aminophenol, i-aminobenzoic, salicylic And sulfanilic acid.

The systematic names of heterofunctional compounds are built according to the general rules of substitutional nomenclature (see 1.2.1). However, for a number of widely used acids, trivial names are preferred (see Table 9.2). Their Latin names serve as the basis for the names of anions and acid derivatives, which often do not coincide with Russian trivial names.

Reactivity

PROGRAM

course in organic chemistry

for students of the Faculty of Biology and Soil

INTRODUCTION

The subject of organic chemistry. The history of the emergence of organic chemistry and the reasons for its separation into a separate science. Distinctive features of organic compounds and organic reactions.

The structure of organic compounds. Theory of chemical structure. The role of A.M. Butlerov in its creation. Chemical bonds: simple and multiple. Structural formula. Isomerism. Homology. Dependence of chemical properties on the composition and structure of the substance. chemical function. main functional groups.

Classification of organic compounds. Principles of systematic (IUPAC) nomenclature.

Chemical bond in the molecules of organic compounds. Types of chemical bond. Ionic, covalent, coordination bonds. Semipolar connection. The role of the electronic octet. Electronic configurations of elements. Atomic orbitals and valence states of carbon. Hybridization of atomic orbitals: sp3,sp2, sp(three valence states of a carbon atom). s- and p-bonds. The main parameters of a covalent bond are: bond energy, bond length, bond polarity and polarizability. The electronegativity of the elements. The concept of mesomerism (resonance). Electronic substituent effects: inductive ( I), mesomeric ( M).

Isomerism of organic compounds. Structural isomers and stereoisomers. Fundamentals of stereochemistry. Spatial structure of methane and its homologues. The principle of free rotation and the limits of its applicability. Shielded and hindered conformations. Conformations of open chain compounds. Conformational formulas of Newman and "goat" type. Conformation of the cyclohexane ring. Axial and equatorial connections. Inversion of the chair conformation. Comparison of stability of cyclohexane derivatives with axial and equatorial positions of substituents. 1,3-Diaxial interaction.

Geometric ( cis - trans) isomerism and the conditions for its appearance in the series of olefins, cycloalkanes. E-, Z- nomenclature.

Optical isomerism. Optical activity and optically active substances. Molecular asymmetry as a condition for the appearance of optical activity. Asymmetric carbon atom. Enantiomers and diastereomers. R- And S- nomenclature to designate the configuration of the center of chirality. Fisher projection formulas. D- and L-nomenclature. Stereoisomerism of compounds with several centers of chirality. Erythro- and threoisomers. Mesoforms. racemic modification.

Classification of organic reactions according to the nature of the transformations and the nature of the reagents.

HYDROCARBONS

Alkanes. Homologous series of methane. Isomerism. Nomenclature. Ways to get. Physical properties, their dependence on chain length and structure. Chemical properties. Radical substitution reactions (S R): halogenation (influence of the nature of the halogen), nitration (Konovalov), sulfochlorination, oxidation. Initiation and inhibition of radical reactions. Reactivity of hydrogen atoms associated with primary, secondary and tertiary carbon atoms. Alkyl radicals and their relative stability.

Alkenes. Isomerism. Nomenclature. Ways to get. physical properties. Length and energy of double bond formation. Chemical properties. Electrophilic addition reactions: halogens, hydrogen halides, water, hypohalic acids, sulfuric acid. The mechanism of electrophilic addition reactions. Stereo- and regional orientation of accession. Carbocations, their stability depending on the structure. Markovnikov's rule and its modern justification. Radical addition: addition of HBr in the presence of peroxides. Nucleophilic addition. Polymerization: cationic, anionic and radical. catalytic hydrogenation. Oxidation: epoxidation according to Prilezhaev, oxidation with potassium permanganate, ozonation. Chemical properties of the a-methylene link adjacent to the p-bond (allylic position): chlorination, oxidation.

Alkynes. Isomerism. Nomenclature. Syntheses of acetylene and its homologues. Characterization of physical properties. Chemical properties of acetylenes: addition reactions, substitution reactions involving a mobile hydrogen atom at carbon with a triple bond. Acetylides. Polymerization of acetylene to benzene, vinylacetylene, cyclooctatetraene.

Alkadienes. Types of alkadienes. Isomerism. Nomenclature. Stereochemistry of allenes. Molecular asymmetry. Conjugated - 1,3-dienes. Methods for obtaining dienes. physical properties. Lengths of carbon-carbon bonds in 1,3-butadiene and its energy of formation. Manifestation of the effect of conjugation. 1,2- and 1,4-addition to 1,3-dienes - electrophilic addition of halogens and hydrogen halides. Carbocations of the allyl type. Cycloaddition to a diene system: Diels-Alder diene synthesis. Polymerization of 1,3-dienes. Synthetic rubber based on 1,3-butadiene (divinyl). Copolymers of divinyl with styrene, acrylonitrile, butyl rubber. Natural rubber: its structure, ozonolysis, processing into rubber.

Cycloalkanes. Classification. Isomerism. Nomenclature. General and special methods for the synthesis of small, medium and large cycles. Physical and chemical properties. Comparative evaluation of the reactivity and thermal stability of cyclopropane, cyclobutane, cyclopentane and cyclohexane. Bayer's stress theory and its modern understanding. Estimation of intensity of cycles on the basis of heats of combustion. Modern understanding of the structure of cyclopropane. Conformations of cycloalkanes. Cycloalkenes and cycloalkadienes.

aromatic hydrocarbons. Features of the chemical properties of benzene and its homologues. The structure of benzene (valence angles, interatomic distances). Energy of formation and heat of hydrogenation of benzene. stabilization energy. Aromatic character of the benzene ring. Modern conception of the nature of aromaticity. Non-benzenoid aromatic compounds. Hückel's aromaticity rule. Aromaticity of heterocyclic compounds: furan, thiophene, pyrrole, pyridine. Aromaticity of cyclopropenyl cation, cyclopentadienyl anion, cycloheptatrienyl cation. Lack of aromatic properties in cyclooctatetraene.

Benzene homologues. Homologous series of benzene. Isomerism in the series of alkylbenzenes. Nomenclature. Laboratory methods of synthesis. Production methods in industry. Reactions of electrophilic substitution in the aromatic nucleus. General patterns and mechanism of these reactions. electrophilic reagents. Halogenation, nitration, sulfonation, alkylation, acylation. Influence of electron-donating and electron-withdrawing substituents (activating and deactivating) on ​​the direction and rate of electrophilic substitution in the benzene nucleus. Influence of inductive and mesomeric effects of substituents. Substitution Orientation Rules: ortho- And pair- orientants (substituents of the first kind) and meta- orientants (substituents of the second kind). Coordinated and non-coordinated orientation. Halogenation and oxidation of side chains.

Polynuclear aromatic hydrocarbons.

a) Hydrocarbons with non-condensed nuclei. Diphenyl. diphenylmethane and triphenylmethane. Triphenylmethyl radical, cation and anion. Reasons for their stability.

b) Hydrocarbons with condensed nuclei. Naphthalene and anthracene. Sources of receipt. Isomerism of monosubstituted derivatives. The structure of naphthalene and anthracene. Addition and substitution reactions. Hydrogenation, oxidation, halogenation, nitration, sulfonation. Comparative evaluation of the aromatic character of benzene, naphthalene and anthracene. Phenantrene. Distribution of the phenanthrene skeleton in natural compounds.

HYDROCARBON DERIVATIVES

Halogen derivatives.

a) Alkyl halides. Isomerism. Nomenclature. Production methods: direct halogenation of alkanes, addition of hydrogen halides to alkenes and alkynes, from alcohols by the action of phosphorus halide derivatives. Physical and chemical properties. Reactions of nucleophilic substitution of halogen. Mechanisms of S N 1 and S N 2, stereochemistry of reactions. Nucleophile. Leaving group. Formation, stabilization and rearrangement of carbonium ions. Dependence of the reaction mechanism on the structure of the halogen derivative and on the nature of the solvent. Comparison of S N 1 and S N 2 reactions. Reactions of elimination of hydrogen halides (E1 and E2): stereochemistry, direction of elimination. Zaitsev's rule. Competition between substitution and elimination reactions depending on the nature of the reagent and reaction conditions. Reactions of alkyl halides with metals. Grignard reagents: preparation and properties.

b) Aromatic halogen derivatives (Aryl halides). Nomenclature. Preparation: direct halogenation to the core, from diazonium salts. Chemical properties. Reactions of electrophilic substitution (influence of halogens). Reactions of nucleophilic substitution in halogenaryls.

ALCOHOL

Monohydric saturated alcohols. Isomerism. Nomenclature. Obtaining: from alkyl halides, hydration of alkenes, reduction of carbonyl compounds. Obtaining primary, secondary and tertiary alcohols using Grignard reagents (synthesis planning and limitations). physical properties. Association. Hydrogen bond. Chemical properties of alcohols. Acid-base properties of alcohols. Reactions involving the О-Н bond: the action of metals and organometallic compounds, the formation of esters of mineral acids, the esterification reaction. Reactions involving the C-OH bond and their mechanism: substitution of hydroxyl for halogen. Dehydration of alcohols - intramolecular and intermolecular. Reaction mechanism, Zaitsev-Wagner rule. Dehydrogenation and oxidation of alcohols.

Dihydric alcohols (glycols). Classification, isomerism. Nomenclature. Methods for obtaining glycols. Features of physical and chemical properties. dehydration of glycols. Pinacol rearrangement. Oxidation reactions.

polyhydric alcohols. Glycerol. Synthesis. Chemical properties and applications. Nitroglycerine. Polyhydric alcohols: erythritols, pentites, hexites.

PHENOLS

Monohydric phenols. Isomerism, nomenclature. Industrial production methods: alkaline smelting of sulfonates, hydrolysis of aryl halides, cumene oxidation. Preparation from diazonium salts. Chemical properties. Acidity of phenols. Reactions involving the O-H bond: the formation of phenolates, ethers and esters. Williamson reaction. Mutual influence of hydroxyl groups and the aromatic nucleus of phenol. Electrophilic substitution reactions: halogenation, sulfonation, nitration, combination with diazo compounds. Condensation of phenol with formaldehyde. Oxidation and reduction of phenols.

polyhydric phenols. Pyrocatechin, resorcinol, hydroquinone.

ETHERS

Classification. Isomerism. Nomenclature. Receiving methods. Physical and chemical properties. Formation of oxonium compounds. Substitution of the alkoxy group in ethers (cleavage of ethers).

Cyclic ethers. Epoxy. Receipt. Chemical properties of epoxides. Ring opening reactions catalyzed by acids and bases (reaction mechanism, stereochemistry, direction of ring opening), reaction with organometallic compounds. Tetrahydrofuran. Dioxane.

Amines. Primary, secondary and tertiary amines. Amines, aliphatic and aromatic. Isomerism and nomenclature. Methods for the synthesis of amines. Physical and chemical properties of amines. Basic character of amines. Influence of the nature and number of alkyl or aryl groups in an amine on its basicity. Alkylation of amines. Quaternary ammonium bases and their salts. Acylation of amines. Properties and applications of acyl derivatives. Reactions of electrophilic substitution in a number of aromatic amines: halogenation, nitration, sulfonation. Amides of sulfanilic acid (sulfanilamide preparations). The action of nitrous acid on primary, secondary and tertiary amines of the aliphatic and aromatic series.

Aromatic diazo compounds. diazotization reaction. Conditions for carrying out and reaction mechanism. Diazonium cation: stability and electrophilic character. Reactions of diazo compounds with nitrogen evolution: substitution by halogen, hydroxyl, cyano group, hydrogen and other atoms and groups. Reactions of diazo compounds without nitrogen evolution. Azo coupling reaction as an electrophilic substitution reaction. flow conditions. Azo dyes - oxyazo- and aminoazo compounds. Indicator properties of azo dyes on the example of methyl orange. Relationship between color and texture. Recovery of diazo compounds.

Amino alcohols. Ethanolamine (colamine). Choline. Acetylcholine. Sphingosine.

CARBONYL COMPOUNDS

Limit aldehydes and ketones(derivatives of alkanes, cycloalkanes and aromatic hydrocarbons). The structure of the carbonyl group. Isomerism. Nomenclature. Industrial production of formaldehyde from methyl alcohol, acetaldehyde from acetylene. General methods for the preparation of aldehydes and ketones. Chemical properties. Comparison of the reactivity of aldehydes and ketones (aliphatic and aromatic). Nucleophilic addition at the carbonyl group: water, alcohols, hydrocyanic acid, sodium bisulfite, organomagnesium compounds. General scheme of reactions with ammonia derivatives. Reactions with amines, hydroxylamine, hydrazines, semicarbazide. Acid and basic catalysis of addition reactions. Recovery of carbonyl compounds to alcohols, hydrocarbons. Oxidation of aldehydes and ketones. Disproportionation reactions (Cannizzaro, Tishchenko). Reactions involving hydrogen a-carbon atom. Halogenation. haloform reaction. Aldol seal. The mechanism of the reaction and the role of the catalyst. Croton condensation.

Unsaturated carbonyl compounds. a-,b-Unsaturated aldehydes and ketones. Receipt. Conjugation of a carbonyl group and a double bond. Addition reactions of electrophilic and nucleophilic reagents. polymerization. Acrolein. Crotonaldehyde.

carboxylic acids

monocarboxylic acids. Isomerism Nomenclature. Synthesis methods. physical properties. The structure of the carboxyl group. acid properties. acidity constant. Influence of the effect of substituents on the strength of carboxylic acids. Reactions that take place with a break in the O-H bond. Salts of carboxylic acids. Reactions that take place with a break in the C-OH bond: the formation of functional derivatives of carboxylic acids. Esterification reaction and its mechanism. Equilibrium constant. Preparation of acid halides, anhydrides and amides. The mechanism of the nucleophilic substitution reaction in acids and their derivatives. Comparison of the reactivity of acid derivatives in reactions with nucleophilic reagents. Acid halides. Chemical properties. Interaction with water, ammonia, amines, alcohols. Acylation reactions. Amides. Reduced basicity of amides. Hydrolysis of amides in acidic and alkaline media. Dehydration. Amide bond in protein molecules. Complex ethers. Chemical properties. Hydrolysis of esters and its mechanism. transesterification reaction. Interaction with the Grignard reagent. Recovery of esters. Nitriles. Hydrolysis and reduction to amines. Reactions of acids involving hydrogen at a-carbon atom: halogenation, oxidation. Decarboxylation of carboxylic acids.

Unsaturated monocarboxylic acids. Isomerism. Nomenclature. Mutual influence of double bond and carboxyl group. Addition of electrophilic and nucleophilic reagents. Higher unsaturated fatty acids: oleic, linoleic acid. Esters of higher fatty acids and glycerol are fats. Vegetable oils and their types. The structure of natural glycerides and their properties. Configuration of natural triacylglycerols containing an asymmetric carbon atom. hydrolysis of fats. Soap. Hydrogenation of fats. Lipids. Glycolipids. Glycerophospholipids. Ethanolamine phosphoglycerides (cephalins). Cholinephosphoglycerides (lecithins).

dicarboxylic acids. Isomerism. Nomenclature. Synthesis methods. Physical and chemical properties. Dissociation steps and acidity constants. Formation of two series of functional derivatives. Relation to heating oxalic, malonic, succinic, glutaric and phthalic acids. cyclic anhydrides. Phthalimide, potassium phthalimide. Malonic ether. Substitution reactions involving hydrogen atoms of the methylene group. Synthesis of mono- and dibasic acids using malonic ester. Adipic acid. Polycondensation reactions and their use in industry (artificial fiber).

DERIVATIVES OF CARBONIC ACID

Phosgene. Synthesis, properties and application. Esters of chlorocarbonic and carbonic acids. Carbamic acid: carbamates, esters (urethanes). Urea. Synthesis methods. Structure and reactions. Biuret. Acylation of urea (ureides).

OXYACIDS

Classification. dihydric monobasic acids. Isomerism. Nomenclature. Glycolic acid. Lactic acids and their stereoisomerism. Methods for the synthesis of a-, b- and g-hydroxy acids. Chemical properties. Dehydration of hydroxy acids. lactides and lactones. Dibasic triatomic hydroxy acids. malic acids. Stereoisomerism. The phenomenon of the Waldenian conversion.

Dibasic tetrahydric hydroxy acids. Tartaric acids, their stereoisomerism. Grape and mesotartaric acids. Stereochemistry of compounds with two asymmetric atoms, identical and different. Racemates. Diastereomers. Mesoforms. Aromatic hydroxy acids. Salicylic acid. Receipt and application. Aspirin.

OXO ACIDS (ALDEHYDO AND KETO ACIDS)

Classification. Nomenclature. Glyoxylic and pyruvic acids. Getting and properties. Decarboxylation and decarbonylation. b-Keto acids: acetoacetic acid and its ester. Synthesis of acetoacetic ester. Ester Claisen condensation, its mechanism. Chemical properties of acetoacetic ester. Reactions characteristic of the ketone and enol forms of acetoacetic ester. The phenomenon of tautomerism. Keto-enol tautomerism of acetoacetic ester. Reasons for the relative stability of the enol form. Acid and ketone cleavage of acetoacetic ester. Synthesis of ketones, mono- and dicarboxylic acids.

Similar information.

Application. Storage.

quantitation

Goodness

Authenticity

Receipt

Iron preparations

Application. Storage.

store in a well-closed container, in a cool place, since sodium tetraborate can lose water of crystallization and hydrolyze to form boric acid:

Na 2 B 4 O 7 + 7 H 2 O ® 4 H 3 BO 3 ↓ + 2NaOH

Boric acid does not require special storage conditions.

Apply preparations as antiseptics for external use. Boric acid is used in the form of 2-3% solutions for gargling, in the form of glycerin solutions, ointments, powders. 1-2% solutions are used in eye practice. Boron compounds are poisonous, so they are not used internally. Borax is used in the form of 1-2% solutions.

Description. Solubility. Prismatic transparent crystals of light bluish-green color or crystalline pale green powder. Soluble in water, slightly acid solutions. It vanishes in the air.

An excess of reduced iron is dissolved in a 30% solution of sulfuric acid at t o \u003d 80 o C: Fe + H 2 SO 4 ® FeSO 4 + H 2

The solution is evaporated, the drug is dried at t o = 30 o C.

Carry out pharmacopoeial reactions to the iron ion and sulfate ions.

1) Fe2+: Turnbull blue formation reaction:

FeSO 4 + K 3 + H 2 SO 4 ® FeK ¯ + 2 K 2 SO 4

Reaction with alkali and ammonia solutions:

FeSO 4 + NaOH + NH 4 OH ® Fe (OH) 2 ¯ + O 2 air. ® Fe(OH) 3 ¯

white brown

Sulfide precipitation reaction:

FeSO 4 + Na 2 S ® FeS ¯ + Na 2 SO 4

2) SO 4 2-: FeSO 4 + BaCl 2 ® BaSO 4 ¯ + FeCl 2

1) allowed: heavy metals, As.

2) unacceptable: copper salts are opened by adding H 2 O 2 and NH 4 OH, then the precipitate formed is filtered off; the filtrate should be colorless.

permanganatometry, direct titration. The method is based on the oxidation of Fe(II) with potassium permanganate in an acid medium to Fe(III). E = M.

10 FeSO 4 + 2 KMnO 4 + 8 H 2 SO 4 ® 5 Fe 2 (SO 4) 3 + K 2 SO 4 + 2 MnSO 4 + 8 H 2 O

store in a well-closed container, in a dry place, avoiding loss of water of crystallization and oxidation in humid air with the formation of the basic salt Fe 2 (OH) 4 SO 4 . At 64°C, iron sulfate melts in its crystalline water.

Apply ferrous sulfate in the complex therapy of iron deficiency anemia in the form of tablets and injections. Assign 0.05–0.3 g per reception.

Carbonic acid forms two types of salts: medium - carbonates and acidic - bicarbonates.

NaHCO3

Sodium Hydrocarbonate Natrii hydrocarbonas

Description. Solubility. Odorless white crystalline powder, saline-alkaline taste, soluble in water, practically insoluble in alcohol. Aqueous solutions have a slightly alkaline reaction. When shaking and heating up to 70 ° C aqueous solutions of NaHCO 3, a double salt of Na 2 CO 3 is formed · NaHC03.