Reaction of acetic acid with phosphorus chloride 5. Chemical properties

Grade 11

Option 1

A. C 2 H 5 SON B. HCOOH

B. C 2 H 5 COOSH 3 G. CH 3 OH

2. Write the reaction equation:

A. Ethanol with propionic acid

B. Oxidation of formic aldehyde with copper (II) hydroxide.

B. Ethyl ester of acetic acid with sodium hydroxide.

CH 4 → C 2 H 2 → CH 3 COH → CH 3 COOH → (CH 3 COO) 2 Mg.

4. Calculate the mass of acid obtained by heating 55 g of a 40% ethanal solution with an excess of copper (II) hydroxide

Independent work on the topic “Oxygen-containing organic compounds”Grade 11

Option 2

1. Define classes of compounds, give the names of substances whose formulas are:

A. CH 2 OH-CHON-CH 2 OH B. C 6 H 5 -CH 2 OH

B. CH 3 OCH 3 D. CH 3 COO CH 3

A. Propionic acid with sodium hydroxide.

B. Acetic acid with phosphorus chloride (5).

B. Hydrolysis of propyl ether acetic acid(propyl ethanoate).

Indicate their type, conditions of implementation and name starting materials and reaction products.

3. Write reaction equations that can be used to carry out transformations according to

CH 4 → CH 3 C1 → CH 3 OH → HSON → HCOOH.

Indicate the conditions for the reactions and the names of all substances.

4. Calculate the mass of 60% acetic acid required to neutralize 120 g of 25% sodium hydroxide solution.

Independent work on the topic “Oxygen-containing organic compounds”Grade 11

Option 3

1. Define classes of compounds, give the names of substances whose formulas are:

A. C 3 H 7 COOH. B. C 2 H 5 OH

B. NSOOSN 3. G. C 6 H 5 OH.

2. Write the reaction equations:

A. Formic acid with magnesium oxide.

B. Intermolecular dehydration of propanol-1 alcohol.

B. Hydrolysis of tristearic fat.

Indicate their type, conditions of implementation and name the starting materials and reaction products.

3. Write reaction equations that can be used to carry out transformations

according to the diagram:

C 2 H 6 → C 2 H 5 Br → C 2 H 5 OH → CH 3 COH → CH 3 COOH.

Indicate the conditions for the reactions and the names of all substances.

4. Calculate the mass of metallic silver obtained by oxidation of 600 g of 40%

excess formaldehyde solution ammonia solution silver oxide.

Methods of obtaining. 1 . Oxidation of aldehydes and primary alcohols - general method receiving carboxylic acids. />K M n O 4 and K 2 C r 2 O 7 are used as oxidizing agents.

2 Another common method is the hydrolysis of halogenated hydrocarbons containing three halogen atoms per carbon atom. In this case, alcohols containing OH groups on one carbon atom are formed - such alcohols are unstable and split off water to form a carboxylic acid:

3. Obtaining carboxylic acids from cyanides (nitriles) is important way, allowing the carbon chain to be extended when producing the starting cyanide. An additional carbon atom is introduced into the molecule using the reaction of replacing a halogen in a halocarbon molecule with sodium cyanide, for example:

CH 3 -B r + NaCN→ CH 3 - CN + NaBr.

The resulting acetic acid nitrile (methyl cyanide) easily hydrolyzes when heated to form ammonium acetate:

CH 3 CN + 2H 2 O → CH 3 COONH 4.

When the solution is acidified, acid is released:

CH 3 COONH 4 + HCl→ CH 3 COOH + NH 4 Cl.

4 . Usage Grignard reagent according to the scheme:/>

H 2 O
R— MgBr+ CO 2 → R — COO — MgBr→ R - COOH + Mg (OH) Br

5 . Hydrolysis of esters:/>

R - COOR 1 + KON → R - COOK + R'OH,

R - COOK + HCl → R— COOH+ KCl .

6. Hydrolysis of acid anhydrides:/>

(RCO) 2 O + H 2 O → 2 RCOOH.

7. There are specific methods of preparation for individual acids./>

Formic acid is prepared by heating carbon monoxide ( II ) with powdered sodium hydroxide under pressure and treating the resulting sodium formate with a strong acid:

Acetic acid is produced by the catalytic oxidation of butane with atmospheric oxygen:

2C 4 H 10 + 5 O 2 → 4CH 3 COOH + 2H 2 O.

To obtain benzoic acid, you can use the oxidation of monosubstituted benzene homologues with an acidic solution of potassium permanganate:

5C 6 H 5 -CH 3 + 6 KMnO 4 + 9 H 2 SO 4 = 5C 6 H 5 COOH + 3 K 2 SO 4 + 6 MnSO 4 + 14 H 2 O.

Additionally, benzoic acid can be prepared from benzaldehyde using Cannizzaro's reactions. In this reaction, benzaldehyde is treated with 40-60% sodium hydroxide solution at room temperature. Simultaneous oxidation and reduction leads to the formation benzoic acid and, accordingly, phenylmethanol (benzyl alcohol):

Chemical properties . Carboxylic acids are stronger acids than alcohols because the hydrogen atom in the carboxyl group has increased mobility due to the influence of the CO group. In an aqueous solution, carboxylic acids dissociate:

RCOOH RCOO—+H+

However, due to the covalent nature of carbon molecules y acids, the above dissociation equilibrium is sufficient strongly shifted to the left. Thus, carboxylic acids - this is usually weak acids. For example, ethane (acetic)the acid is characterized by a dissociation constant K a = 1.7*10 -5./>

Substituents present in a carboxylic acid molecule greatly influence its acidity due to the effect they have inductive effect. Substituents such as chlorine or phenyl radical attract electron density and, therefore, cause a negative inductive effect(-/). The withdrawal of electron density from the carboxyl hydrogen atom leads to an increase in the acidity of the carboxylic acid. acids. In contrast, substituents such as alkyl groups have electron-donating properties and create a positive inductive effect, +I. They reduce acidity. Effect of substituents on the acidity of carboxylic acidsclearly manifested in the values ​​of dissociation constants K a for a number of acids. In addition, the strength of the acidis influenced by the presence of a conjugate multiple bond.

The mutual influence of the atoms in the molecules of dicarboxylic acids leads to the fact that they are stronger than monobasic acids.

2. Formation of salts. Carboxylic acids have all the properties of ordinary acids. They react with active metals, basic oxides, bases and salts of weak acids:

2 RCOOH + M g → (RCOO) 2 Mg + H 2,

2 RCOOH + CaO → (RCOO) 2 Ca + H 2 O,

RCOOH+ NaOH → RCOONa+ H 2 O,

RCOOH+ NaHCO 3 → RCOONa+ H 2 O + CO 2.

Carboxylic acids are weak, so strong mineral acids displace them from the corresponding salts:

CH 3 COONa + HCl→ CH 3 COOH + NaCl.

Salts of carboxylic acids in aqueous solutions are hydrolyzed:

CH 3 COOK + H 2 O CH 3 COOH + CON.

The difference between carboxylic acids and mineral acids is the possibility of forming a number of functional derivatives.

3. Formation of functional derivatives of carboxylic acids. When replacing the OH group in carboxylic acids with various groups (/>X ) functional derivatives of acids are formed, having the general formula R-CO-X; here R means an alkyl or aryl group. Although nitriles have a different general formula ( R-CN ), they are usually also considered to be derivatives of carboxylic acids, since they can be prepared from these acids.

Acid chlorides are produced by the action of phosphorus chloride ( V) for acids:

R-CO-OH + PC l 5 → R-CO- Cl+ ROS l 3 + HCl.

Anhydrides are formed from carboxylic acids under the action of water-removing agents:

2 R - CO - OH + P 2 O 5 → (R - CO -) 2 O + 2HPO 3.

Esters are formed by heating an acid with an alcohol in the presence of sulfuric acid ( reversible reaction esterification):

The mechanism of the esterification reaction has been established by the "labeled atoms" method.

Esters can also be obtained by reacting acid chlorides and alkali metal alcoholates:

R-CO-Cl + Na-O-R’ → R-CO-OR’ + NaCl .

Reactions of carboxylic acid chlorides with ammonia lead to the formation of amides:

CH 3 -CO-C l + CH 3 → CH 3 -CO-CH 2 + HCl.

In addition, amides can be prepared by heating ammonium salts of carboxylic acids:

When amides are heated in the presence of dewatering agents, they dehydrate to form nitriles:

Functional derivatives of lower acids are volatile liquids. All of them are easily hydrolyzed to form the parent acid:

R-CO-X + H 2 O → R-CO-OH + HX.

In an acidic environment these reactions can be reversible. Hydrolysis in an alkaline environment is irreversible and leads to the formation of carboxylic acid salts, for example:

R-CO-OR ‘ + NaOH → R-CO-ONa + R’OH.

4 . A number of properties of carboxylic acids are due to the presence of a hydrocarbon radical. Thus, when halogens act on acids in the presence of red phosphorus, halogen-substituted acids are formed, and the hydrogen atom at the carbon atom (a-atom) adjacent to the carboxyl group is replaced by halogen:

Unsaturated carboxylic acids are capable of addition reactions:

CH 2 = CH-COOH + H 2 → CH 3 -CH 2 -COOH,

CH 2 =CH-COOH + C l 2 → CH 2 C l -SHC l -COOH,

CH 2 =CH-COOH + HCl → CH 2 C l -CH 2 -COOH,

CH 2 = CH-COOH + H 2 O → HO-CH 2 -CH 2 -COOH,

The last two reactions proceed against Markovnikov's rule.

Unsaturated carboxylic acids and their derivatives are capable of polymerization reactions.

5 . Redox reactions of carboxylic acids./>

Carboxylic acids, under the action of reducing agents in the presence of catalysts, can be converted into aldehydes, alcohols and even hydrocarbons:

Formic acid HCOOH has a number of features, since it contains an aldehyde group:

Formic acid is a strong reducing agent and is easily oxidized to CO 2 . She gives "silver mirror" reaction:

HCOOH + 2OH → 2Ag + (NH 4) 2 CO 3 + 2NH 3 + H 2 O,

or in simplified form:

C H 3 HCOOH + Ag 2 O → 2Аg + CO 2 + H 2 O.

In addition, formic acid is oxidized by chlorine:

HCOOH + Cl 2 → CO 2 + 2 HCl.

In an oxygen atmosphere, carboxylic acids are oxidized to CO 2 and H 2 O:

CH 3 COOH + 2O 2 → 2CO 2 + 2H 2 O.

6. Reactions decarboxylation. Saturated unsubstituted monocarboxylic acids due to their high strength S-S connections When heated, they decarboxylate with difficulty. This requires melting the salt. alkali metal carboxylic acid with alkali:/>

The appearance of electron-donating substituents in the hydrocarbon radical promotes decarboxylation reactions:

Dibasic carboxylic acids easily split off CO 2 when heated:

Carboxylic acids form a variety of derivatives (esters, anhydrides, amides, etc.), which participate in many important reactions. General formula derivatives of carboxylic acids:

where the acyl radical can be linked to residues ( X) alcohol, ammonia, carboxylic acid and other compounds, forming the corresponding derivatives.

4.2.2.1 HALONAHYDRIDES– (acyl halides) of acids are considered functional derivatives that are obtained by substitution HE-carboxyl groups on halogen. The simplest carboxylic acid halides are liquids with a pungent odor. They react vigorously with water, forming the corresponding carboxylic acids. Due to low mobility HE-groups in carboxyl, this substitution is carried out by the interaction of carboxylic acids with phosphorus halides or thionyl chloride as stronger nucleophiles.

Methods of obtaining

1. Interaction with phosphorus (V) chloride:

2. Interaction with thionyl chloride:

Characteristics of reactivity. Acid halides are compounds with high reactivity. They easily exchange halogen for nucleophilic groups, since at the reaction center ( WITH-atom of the carbonyl group) there is a deficiency of electrons, these transformations can be attributed to S N reactions.

Acyl halides are characterized by high bond polarity, which is caused by the electron-withdrawing effect of the halogen atom.

The electron density on the carbon atom of the carboxyl group is greatly underestimated. Acyl halides have strong electrophilic properties.

Chemical properties. Acid chlorides are used as acylating agents to introduce an acyl radical into various classes of organic compounds.

1. Hydrolysis:

2. Alcoholism:

3. Acidolysis:

4. Ammonolysis:

5. Preparation of acyl peroxides. Acyl peroxide is formed by the reaction of solutions of acetyl chloride in ether or pentane with hydrogen peroxide and sodium hydroxide or with metal peroxides (sodium or barium peroxides):

6. Reactions with sodium alcoholate and silver acetate:

4.2.2.2 ACID ANHYDRIDES-acid anhydrides can be considered as products of intermolecular dehydration of acids. However, the dehydration reaction occurs only under severe conditions, and most often anhydrides are obtained by the acylation of carboxylic acid salts with acid chlorides, and a mixed anhydride can also be obtained.

Carboxylic acid anhydrides are colorless liquids or crystalline substances. Anhydrides of lower carboxylic acids are liquids with a pungent odor that boil at a temperature higher than their corresponding acids. Anhydrides are poorly soluble in water. An aqueous solution of acetic anhydride hydrolyzes slowly.

Methods of obtaining

Acidolysis of carboxylic acids:

Chemical properties

1. Use of anhydrides as acylating agents. Anhydrides, like acid halides, have great chemical activity and are good acylating agents (part 1, chapter 8.5.2, part 2, chapter 2, 3.3, part 3, chapter 1), entering into the same reactions as acid halides, however less energetic:

4.2.2.3 CARBOXYLIC ACIDS AMIDES– functional derivatives of acids in which the hydroxyl of the carboxyl group is replaced by an amino group. In amides, the hydrogen atoms in the amino group can be replaced by hydrocarbon radicals. In this case they are called N-alkyl- or N-arylamides. Amides can also be considered as derivatives of ammonia, in which the hydrogen atom is replaced by an acyl residue.

Amides are colorless crystalline substances or liquids that dissolve in water and organic solvents. Amides whose molecules contain bonds N–H, are associated due to the formation of intermolecular hydrogen bonds and have more high temperatures boiling.

In the amide group, the bonds are delocalized due to their flat structure and the presence n,π -conjugate system. This leads to a redistribution of electron density: on the nitrogen atom the electron density decreases compared to ammonia and amines, and on the carbon atom it increases compared to aldehydes and ketones. Amides with low molecular weight highly polar and highly soluble in water. They are often used as solvents.

In amide molecules there is a significant interaction between NEP nitrogen atom and π -electronic system double bond C=O. A conjugate system of connections is formed, the nature of the connections changes C–N And C–O and electron density distribution. As a result, the connection C–N becomes shorter, and the connection C=O slightly longer compared to unconjugated compounds:

Comparison of the basic properties of amines and amides. The basicity of amides is less than that of ammonia and aliphatic amines. In the amide molecule there are two main centers of electrophilic attack - nitrogen and oxygen atoms, to which a proton can attach. On the nitrogen atom, the electron density is reduced and the proton attack on oxygen is more advantageous, which preserves a stable conjugated bond system.

Amides containing N– H bonds, have slightly acidic properties, but are stronger acids than ammonia. In aqueous solution, amides give a neutral reaction. However, when interacting with active metals amides containing N– H bonds, abstract a proton, since this results in the formation of an amide anion stabilized by delocalization of a negative charge.

In cyclic amides (imides), the acidity is more pronounced, since the nitrogen atom is under the influence of two carbonyl groups.

Compared to amines, carboxylic acid amides are weak grounds due to the strong interaction of the lone electron pair of the nitrogen atom with the carbonyl group.

Methods for preparing amides

CH3COOH + PCl5 = CH3COCl(acetyl chloride) + POCl3(phosphorus chloride) + HCl. You are on the page of the question "write the reaction equation. a) propyl acid with sodium hydroxide b) acetic acid with phosphorus chloride (5) c). The text is available under the Creative Commons Attribution-ShareAlike license; c in some cases can act additional conditions. Carboxylic acids have all the properties of ordinary acids. Questions - leaders Who knows or can create a very smelly and persistent smell that could be sprayed or anointed and the smell would not vent 1 bet. Material from Wikipedia - the free encyclopedia. Acetylation with acetyl chloride is often carried out in the presence of inorganic bases: sodium hydroxide, carbonate or acetate - Schotten-Baumann reaction or tertiary amines pyridine triethylamine - Einhorn modification activate acetyl chloride due to the formation of acetylammonium salts and neutralize the resulting HCl. Interaction with phosphorus chloride V: Due to the electron-withdrawing effect of the carboxyl group COOH, the hydrogen atoms at the carbon in the -position are quite mobile and can be replaced by chlorine or bromine atoms:. Methods of synthesis In industry, acetyl chloride is synthesized by the reaction of acetic acid with phosphorus chlorides, phosphorus trichloride or phosphorus pentachloride: Organic plz help vn koko channel Student closed 6 years ago Added 6 years. Compared to amines, carboxylic acid amides are weak bases due to strong interaction unshared electron pair nitrogen atom with a carbonyl group. Let us denote the amounts of substances acetic acid and formic acid:. Amides are colorless crystalline substances or liquids that dissolve in water and organic solvents. In industry, acetyl chloride is synthesized by the reaction of acetic acid with phosphorus chlorides: phosphorus trichloride or phosphorus pentachloride:. Irina Ruderfer Higher intelligence 6 years ago in the interaction of acetic acid with sodium metal: Tell me how to solve these inequalities 1 bet. General formula of carboxylic acid derivatives:

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Acetyl chloride is also used for acetylation aromatic compounds according to Friedel-Crafts. The white residue after calcination is Na 2 CO 3 soda. Write down the equations for the reactions of benzoic acid in which the C-OH bond in the carboxyl group is cleaved. Acid chlorides are obtained by the action of phosphorus chloride V on acids: Let us denote the amounts of substances acetic acid and formic acid:. In industry, acetyl chloride is synthesized by the reaction of acetic acid with phosphorus chlorides: phosphorus trichloride or phosphorus pentachloride:. When amides are heated with water-removing agents, for example, with phosphorus pentoxide P 2 O 5, carboxylic acid nitriles are formed:

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