Ketones. Presentation on chemistry "ketones" Presentation of aldehydes and ketones

C=O The oxygen and carbon atoms in the carbonyl group are in sp 2 hybridization. The electron density is shifted towards the oxygen atom - I; - M" title="Structure of the C=O group. The properties of aldehydes and ketones are determined by the structure of the carbonyl group >C=O. The oxygen and carbon atoms in the carbonyl group are in sp 2 hybridization. The electron density is shifted to the oxygen atom - I; - M" class="link_thumb"> 4 !} The structure of the C=O group. The properties of aldehydes and ketones are determined by the structure of the carbonyl group >C=O. The oxygen and carbon atoms in the carbonyl group are in sp 2 hybridization. The electron density is shifted towards the oxygen atom - I; - M C=O The oxygen and carbon atoms in the carbonyl group are in sp 2 hybridization. The electron density is shifted towards the oxygen atom - I; - M"> C=O Oxygen and carbon atoms in the carbonyl group are in sp 2 - hybridization. The electron density is shifted to the oxygen atom - I; - M"> C=O Oxygen and carbon atoms in the carbonyl group are in sp 2 - hybridization . The electron density is shifted towards the oxygen atom - I; - M" title="Structure of the C=O group. The properties of aldehydes and ketones are determined by the structure of the carbonyl group >C=O. The oxygen and carbon atoms in the carbonyl group are in sp 2 hybridization. The electron density is shifted to the oxygen atom - I; - M"> title="The structure of the C=O group. The properties of aldehydes and ketones are determined by the structure of the carbonyl group >C=O. The oxygen and carbon atoms in the carbonyl group are in sp 2 hybridization. The electron density is shifted towards the oxygen atom - I; - M"> !}

Trivial names Formula/name Trivial name Boiling point HCHO – methanalFormic aldehyde, formaldehyde -21 CH 3 CHO – ethanalAcetaldehyde20 CH 3 CH 2 CHO – propanalPropionic aldehyde48 CH 2 =CHCHO – 2 propenalAcrolein53 CH 3 CH 2 CH 2 CHO – butanal hydrochloricdehyde74 CH 3 CH 2 CH 2 CH 2 CHO – pentanal Valeraldehyde103 C 6 H 5 CHO – benzaldehyde Benzoaldehyde179

C 6 - higher (especially unsaturated or aromatic) - solid, insoluble in water with a floral odor НСО - formaldehyde - gas with a pungent "title="C 1 - gas with a pungent odor C 2 - C 3 - liquids with a pungent odor odor C 4 - C 6 - liquids with an unpleasant odor > C 6 - higher (especially unsaturated or aromatic) - solid, insoluble in water with a floral odor HCOH - formaldehyde - a gas with a pungent" class="link_thumb"> 9 !} C 1 - gas with a pungent odor C 2 - C 3 - liquids with a pungent odor C 4 - C 6 - liquids with an unpleasant odor >C 6 - higher (especially unsaturated or aromatic) - solid, insoluble in water with a floral odor НСО - formaldehyde – a gas with a pungent suffocating odor, highly soluble in water, boiling point. - 19.3C, poisonous. A 40% solution of formaldehyde is called formalin CH 3 SON - acetaldehyde - a liquid with the smell of green apple, soluble in water t boil. 21C these aldehydes have lower boiling points than the corresponding alcohols C 6 - higher (especially unsaturated or aromatic) - solid, insoluble in water with a floral odor НСО - formaldehyde - a gas with a pungent "> С 6 - higher (especially unsaturated or aromatic) - solid, insoluble in water with a floral odor НСО - formaldehyde - a gas with a sharp suffocating odor, highly soluble in water, boiling point - 19.3 C, poisonous. A 40% solution of formaldehyde is called formalin CH 3 COH - acetaldehyde - a liquid with the smell of a green apple, soluble in water boiling point 21 C in these aldehydes have a lower boiling point than the corresponding alcohols"> C 6 - higher (especially unsaturated or aromatic) - solid, insoluble in water with a floral odor HCOH - formaldehyde - a gas with a sharp " title = " C 1 - gas with pungent odor C 2 - C 3 - liquids with a pungent odor C 4 - C 6 - liquids with an unpleasant odor >C 6 - higher (especially unsaturated or aromatic) - solid, insoluble in water with a floral odor HCOH - formaldehyde - gas with a pungent odor"> title="C 1 - gas with a pungent odor C 2 - C 3 - liquids with a pungent odor C 4 - C 6 - liquids with an unpleasant odor >C 6 - higher (especially unsaturated or aromatic) - solid, insoluble in water with a floral odor НСО - formaldehyde – gas with sharp"> !}

Physical properties of ketones Ketones are volatile liquids. Ketones have a pleasant odor. Higher ketones are solids, lower representatives are highly soluble in water and miscible with organic solvents, some (acetone) are miscible with water in any ratio. The impossibility of forming intermolecular hydrogen bonds causes their volatility to be slightly higher than that of alcohols and carboxylic acids with the same molecular weight (for example, acetone boils at 56.1 °C, and 2-propanol at 82.4 °C) Proponone (dimethyl ketone) or acetone CH 3 -C=O-CH 3 – colorless liquid with a pungent odor, boiling point. 56.24C, highly soluble in water

A distinctive feature of many aldehydes is their smell. Higher aldehydes, especially unsaturated and aromatic ones, are part of essential oils and are found in flowers, fruits, fruits, fragrant and spicy plants. They are used in the food industry and perfumery.

Vanilla buns, cinnamon aroma, Amaretto, chocolate Aldehyde taste melts. In strawberries and coconut, and in jasmine, and in raspberries, and in perfumes, and in food, traces of aldehydes are everywhere. What a smell, what a charm, And where does this freshness come from?! This is a higher aldehyde that gives you its aroma!

CHEMICAL PROPERTIES Addition of hydrosulfites Hydrosulfite derivatives of aldehydes and ketones decompose when heated with acids to form the original carbonyl compounds OH O CH 3 – C – SO 3 Na + HCl CH 3 –C + NaCl + SO 2 + H 2 O H H Grignard reagent Using this reaction, primary alcohol is obtained from formaldehyde, secondary alcohol is obtained from any other aldehyde, and tertiary alcohol is obtained from ketone

Ketones are oxidized under more severe conditions with the cleavage of the C-C bond near the carbonyl group and the formation of a mixture of carboxylic acids. Methyl radicals are oxidized to CO 2 O O CH 3 – C – CH 3 + [O] CH 3 – C + CO 2 OH O 1 O CH 3 – CH 2 – C – CH 3 2CH 3 – C 1 2 OH O 2 CH 3 – CH 2 – C + CO 2 OH OXIDATION OF KETONES

Substitution reactions at the C=O bond 1). With PCl 5, oxygen is replaced by 2 chlorine atoms R R Cl C = O + PCl 5 C R / R / Cl 2). With substances like H 2 NX, oxygen is replaced by NX (NH 3, NH 2 -NH 2, NH 2 – C 6 H 5) R C = O + H 2 – NH C = NH + H 2 O R / 3). the formation of phenol-formaldehyde plastic also occurs through the C=O bond - polycondensation reaction

Test questions 1. Find the formula of the aldehyde: 2. Eliminate the extra substance in the series: 3. Which functional group is called carbonyl? 4. The carbon atom in the aldehyde group is in a state of hybridization: a) sp b) sp 2 c) sp 3 d) not hybridized 5. Name the substances with the formula a) 2-methylbutanone-3, b) 3-methylbutanone-2, c ) 3-methylbutanal, d) 1,2-dimethylpentanal

9. By hydration of which alkyne can an aldehyde be obtained? Write the reaction equation and indicate the conditions for its implementation. a) butanol-2 b) 3-methylbutanol-2 c) 2-methylbutanol-2 d) 2-methylbutanol By heating calcium acetate salts you can get: a) methanal b) ethanal c) propanal d) propanone 11. What signs correctly reflect the physical properties of methanal: 1) colorless liquid, 2) gaseous substance, 3) has a characteristic odor, 4) poorly soluble in water, 5) polar molecule. a) 1, 3, 4 b) 2, 3, 5 c) 3, 4, 5 d) 2, 4, Which of the reactions is named after M. G. Kucherov. a) hydration of acetylene b) trimerization of acetylene c) hydrogenation of acetylene d) bromination of acetylene

Educational presentation on organic chemistry (basic level) “Aldehydes and ketones.” The basic concepts of the topic are presented in a visual form. It can be used in the classroom both when learning new material, and when organizing remote support for studying chemistry, when repeating and consolidating the material covered, and when preparing for test tasks. The material may be useful to teachers, students and their parents.

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and KETONES ALDEHYDES

Acetaldehyde Acetylene Reaction of M. G. Kucherov The hydration reaction of acetylene in the presence of mercury (II) salts leads to the formation of acetaldehyde: The simplest aldehyde is formic aldehyde, or formaldehyde (methanal): General formula of aldehydes:

Aldehydes are carbonyl derivatives of hydrocarbons, the molecules of which contain an aldehyde group: Aldehydes are organic compounds containing a carbonyl group - C = O, bonded to a hydrogen atom and a hydrocarbon radical. Formaldehyde does not fall under this definition because it does not contain a hydrocarbon radical. The name "aldehydes" is explained by the abbreviation of the words "dehydrogenated alcohol"

Ketones General formula of ketones Acetone (dimethyl ketone) is a colorless volatile liquid with a characteristic odor. Solvent, raw material for polymers. Organic compounds containing a carbonyl group – C = O, associated with two hydrocarbon radicals.

Structural features of aldehydes The carbon and oxygen atoms in the carbonyl group are in a state of sp 2 hybridization. Carbon, with its sp 2 hybrid orbitals, forms 3  bonds (one of them is a C–O bond), which are located in the same plane at an angle of about 120° to each other. One of the three sp 2 orbitals of oxygen is involved in the formation of the C–O  bond, the other two contain lone electron pairs. The  bond is formed by the p electrons of the carbon and oxygen atoms.

Physical properties of aldehydes Formaldehyde (methanal, formic aldehyde) is a colorless gas with a pungent odor, highly soluble in water, and very toxic.

Acetaldehyde (ethanal, acetaldehyde) is a volatile liquid, highly soluble in water, with a characteristic odor, poisonous.

Aldehyde nomenclature

Isomerism Interclass isomers of aldehydes are ketones: Carbon skeleton:

Chemical properties of aldehydes

Aldehydes are chemically active substances; upon oxidation, they easily transform into carboxylic acids: Aldehydes react with an ammonia solution of silver (I) oxide, which is used for their qualitative determination of aldehydes: Metallic silver is deposited on the walls of the vessel, forming a layer of metal on the surface, similar on the mirror. Therefore, the qualitative reaction to aldehydes is called the “silver mirror reaction.” + [ O ] Aldehyde Acid + Ag 2 O + + 2Ag ↓ 0 Aldehyde Acid t t

The “silver mirror” reaction

Another qualitative reaction to aldehydes is the oxidation reaction with freshly precipitated copper (II) hydroxide: Acid t + + H 2 O; CuOH yellow t C u 2 O red + H 2 O; +1 +1 С u is an oxidizing agent, reduced to С u + 2 +1 This reaction is called the “color reaction” + 2С u(OH) 2 blue Aldehyde + 2CuOH ↓ +1 yellow + 2

Hydrogenation reaction (hydrogenation) Aldehydes are reduced to the corresponding alcohols - hydrogenated: Aldehyde (alkanal) + H 2 Ni, p, t C pirt (alkanol) + H 2 Ni, p, t Acetaldehyde (ethanal) Ethyl alcohol (ethanol)

Preparation of aldehydes Catalytic dehydrogenation of primary alcohols: Cu, 300 ° C + H 2 In fact, the name “aldehyde” comes from the Latin. and l cohol dehyd rogenatus is alcohol from which hydrogen has been “taken away.” Oxidation of primary alcohols: + [O]t + H 2 O Ethanol Ethanol Acetaldehyde Acetaldehyde

Specific methods of production: Formaldehyde can be obtained by the catalytic oxidation of methane: + O 2 + H 2 O Mn 2+ or Cu 2+, 500 ° C Methane Formaldehyde Acetaldehyde is obtained by the Kucherov reaction: Acetaldehyde Acetylene

In industry, formaldehyde is usually produced in special reactors by passing methyl alcohol vapor with air through a hot copper grid: 2CH 3 OH + O 2  2CH 2 O + 2H 2 O

Application of aldehydes and ketones Methanal (formic aldehyde) CH 2 = O: production of phenol-formaldehyde resins; production of urea-formaldehyde (urea) resins; synthesis of drugs (urotropine); disinfectant; preservative of biological drugs (due to the ability to coagulate proteins). polyoxymethylene polymers; Ethanal (acetic aldehyde, acetaldehyde CH 3 CH = O: production of acetic acid; organic synthesis. Acetone CH 3 - CO - CH 3: solvent for varnishes, paints, cellulose acetates; raw material for the synthesis of various organic substances.

On the topic: methodological developments, presentations and notes

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“Aldehyde class” - Ketones. Use of aldehydes. Oxidation of alcohol with potassium permanganate. Alcohol oxidation. What substances are classified as aldehydes? Interaction with copper hydroxide. Chemical properties of aldehydes. Polycondensation reaction. Acetaldehyde. Physical properties of aldehydes. Aldehyde molecule. Alcohol. Aldehydes.

“Recognition of organic substances” - Residues of substances. Draw a conclusion about the work done. Inscriptions. Do not eat during chemistry experiments. Liquid. Safety regulations. Young chemists. Experiments. Substance. Heating rules. The smell of the substance. Glycerol. Use only clean laboratory glassware. Warning signs.

"Chemistry of amines" - Aniline. Consider methods for producing amines. Substitution reactions of aromatic amines. Determine the formula of the substance. Structure and properties. Isomerism of amines. Application of amines. Preparation of amines. Chemical properties. Aniline is a weaker basic character than ammonia. Methylamine is more basic than ammonia.

“Organic compounds” - Availability of iron to sunflower. Classification scheme of complex compounds of organic substances. System of methods. Concepts explaining the influence of natural EP OPs on the growth and development of plants. Various functional groups. Molecular mass distribution of polluting metals. Some parameters characterizing the entry of 54Mn into corn.

“Aldehyde Lesson” - Addition: hydrogen (hydrogenation) HCOH + H2 -> CH3-OH water (hydration) HCOH + H2O -> HO-CH2-OH. Aldehydes. General formula of aldehydes: O // or CnH2n+1 C\H. Nomenclature. Chemical properties: addition and oxidation reactions. Aldehydes are organic substances whose molecules contain a functional group of atoms - COH, connected to a hydrocarbon radical.

“Nitrogen-containing compounds” - Tetramethylammonium chloride. Azo compounds. Known for his work in the field of aromatic nitro compounds. N-Ethylaniline. Hydrazines. Salazodimethoxin. Methods of obtaining. 1,3-Diaminobenzene (m-phenylenediamine). (Methylethylamine). (CH3)3N. Diazo compounds. Trimethylamine. Azobenzene. 4-Hydroxyazobenzene. CH3NH2.

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The structure of ketones Ketones are organic substances in the molecules of which a carbonyl group is associated with two hydrocarbon radicals. General formula of ketones: Names are derived from the names of the radicals included in their molecule, with the addition of the word ketone, or from the names of the corresponding hydrocarbons, adding the ending - he

Applications Ketones are widely used as industrial solvents for paints, resins, rubbers, tars, varnish, waxes and lubricants. They also serve as chemical intermediates in chemical synthesis and as solvents in the extraction of lubricating oils. Ketones are used as solvents in the production of plastics, rayon, explosives, cosmetics, perfumes and pharmaceuticals. As a solvent, acetone is used in the production of paints, varnishes and drying oils, rubber, plastics, dyes, explosives, and also in photography. It is also used in the production of lubricating oils and in the manufacture of rayon and synthetic leather. In the chemical industry, acetone is a chemical intermediate in the production of many chemicals such as ketene, acetic anhydride, methyl methacrylate, isophorone, chloroform, iodoform and vitamin C.

Applications Methyl ethyl ketone is mainly used for protective coatings and adhesives due to its excellent solvent properties. It is also used as a solvent in magnetic tape production, lubricating oil dewaxing, and food processing. It is a common constituent of varnishes and adhesives and a component of many organic solvent mixtures. Mesityl oxide, methyl butyl ketone and methyl isobutyl ketone are used as solvents in the production of paints, drying oils and varnishes. 4-Methyl-3-pentene-2- it is a component of paints and nail polish removers, as well as solvents for varnishes, inks and enamels. It is also used as an insect repellent, a solvent for nitrocellulose vinyl resins and rubbers, an intermediate in the manufacture of methyl isobutyl ketone, and as a fragrance agent. Methyl butyl ketone is a solvent for nitrocellulose acrylates and alkyd coatings. Methyl isobutyl ketone is a denaturant for alcohol wipes and a solvent for nitrocellulose, varnishes and drying oils, and protective coatings. It is used in the production of methyl amyl alcohol, in the extraction of uranium from fission products, and in the dewaxing of petroleum products.

Applications Halogenated ketones are used in tear gas. Chloroacetone, produced by chlorinating acetone, is also used as a pesticide and in colorants in color photography. Bromoacetone, obtained by treating aqueous acetone with bromine and sodium hypochlorite at temperature, is used in organic synthesis. The alicyclic ketones cyclohexanone and isophorone are used as solvents for a variety of compounds, including resins and nitrocellulose. In addition, cyclohexanone is used as a chemical intermediate in the production of adipic acid for nylon. The aromatic ketones acetophenone and benzoquinone are solvents and auxiliary chemicals. Acetophenone serves as a flavoring agent in perfumes, soaps and creams, and as a flavoring agent in foods, soft drinks and tobacco. Benzoquinone is a rubber vulcanization accelerator, a tanning agent in the leather industry, and an oxidizing agent in the photography industry.