Hydrolysis of organic substances. Hydrolysis Which organic substances react with hydrolysis

Lesson type: a lesson in assimilation of new knowledge and consolidation of the studied material.

Lesson Objectives :

Educational: to form the concept of the hydrolysis of organic substances, to teach how to write equations for the reactions of hydrolysis of various organic substances. To deepen students' knowledge of reversible chemical reactions. Improve skills in working with test tasks different types.

Developing: develop students' ability to compare and analyze theoretical information, apply them in practice, draw conclusions; highlight the main thing in the process of demonstrating experience, develop logical thinking.

Educational: to form a natural-scientific worldview; information culture.

During the classes

Hydrolysis….

What substances?

Lesson topic: "Hydrolysis of organic substances."

Knowing the topic of the lesson, select from the list of words that correspond to this topic (underline them) and give them a definition.

, pyrolysis, polycondensation, water, wax, alkanes, decomposition, exchange, combination.

Find these words in the given text and underline them.

Hydrolysis of organic substances

Living organisms carry out the hydrolysis of various organic substances in the course of reactions starring . For example, during hydrolysis with the participation of digestive enzymes split into , - on the and , (for example, and) - on (for example, on), - on free. Upon hydrolysis in the presence of ; hydrolysis of fats in the presence is used to obtain and. Hydrolysis of wood , and the products are used in the production of feed, , and etc.

Have you defined the words correctly?

Homework:

From scientific text you have chosen words unknown to you, find their definition in information sources and make a dictionary of unknown words.

Make up several tasks (for the ratio) according to the text "Hydrolysis of esters":

Historically, the first example of such a reaction was the alkaline cleavage of higher fatty acid esters, resulting in soap. This happened in 1811, when the French scientist E. Chevreul. heating fats with water in an alkaline medium, he received glycerin and soaps - salts of higher carboxylic acids. Based on this experiment, the composition of fats was established, they turned out to be esters, but only “thrice complex., Derivatives of the trihydric alcohol glycerol - triglycerides. And the process of hydrolysis of esters in an alkaline environment is still called "saponification".

For example, the saponification of an ester formed by glycerol, palmitic and stearic acids:

Sodium salts of higher carboxylic acids are the main components of solid soap, potassium salts are liquid soap.

The French chemist M. Berthelot in 1854 carried out the esterification reaction and synthesized fat for the first time. Consequently, the hydrolysis of fats (as well as other esters) proceeds reversibly. The reaction equation can be simplified as follows:

In living organisms, enzymatic hydrolysis of fats occurs. In the intestine, under the influence of the lipase enzyme, food fats are hydrated into glycerol and organic acids, which are absorbed by the intestinal walls, and new fats characteristic of this organism are synthesized in the body. They travel through the lymphatic system to the bloodstream and then to the adipose tissue. From here, fats enter other organs and tissues of the body, where, in the process of metabolism in cells, they are again hydrolyzed and then gradually oxidized to carbon monoxide and water, releasing the energy necessary for life.

In technology, the hydrolysis of fats is used to obtain glycerol, higher carboxylic acids, and soap.

Used Books:

Textbook “Chemistry Grade 11. A basic level of",O.S. Gabrielyan, Moscow 2007, Bustard.

“Handbook of the teacher. Chemistry Grade 11” Part 1,O.S. Gabrielyan, G.G. Lysova, A.G. Vvedenskaya , M.: 2003, Bustard.

“Getting ready for one state exam. Chemistry”,O.S. Gabrielyan, P.V. Reshetnikov, I.G. Ostroumova, A.M. Nikityuk , M.: 2004, Bustard.

Textbook "Chemistry Grade 11",O.S. Gabrielyan, G.G. Lysova M. : 2002, Bustard.

“Teaching aid in chemistry for specialized training in biomedical classes”, Krasnodar 2008, compiled by professorT.N. Litvinova , head Department of General Chemistry, KSMU.

The hydrolysis of esters proceeds reversibly in an acid medium (in the presence of an inorganic acid) with the formation of the corresponding alcohol and carboxylic acid.

To shift the chemical equilibrium towards the reaction products, hydrolysis is carried out in the presence of alkali.

For example, the saponification of an ester formed by glycerol, palmitic and stearic acids:

Sodium salts of higher carboxylic acids are the main components of solid soap, potassium salts are liquid soap.

In technology, the hydrolysis of fats is used to obtain glycerol, higher carboxylic acids, and soap.

Hydrolysis of carbohydrates

As you gape, carbohydrates are essential components of our food. Moreover, di- (sucrose, lactose, maltose) and polysaccharides (starch, glycogen) are not directly absorbed by the body. They, like fats, first undergo hydrolysis. The hydrolysis of starch proceeds in steps.

In laboratory and industrial conditions, acid is used as a catalyst for these processes. The reactions are carried out with heating.
The reaction of hydrolysis of starch to glucose under the catalytic action of sulfuric acid was carried out in 1811 by the Russian scientist K. S. Kirchhoff.
In humans and animals, hydrolysis of carbohydrates occurs under the action of enzymes (Scheme 4).

Industrial hydrolysis of starch produces glucose and molasses (a mixture of dextrins, maltose and glucose). Molasses is used in confectionery.
Dextrins, as a product of partial hydrolysis of starch, have an adhesive effect: they are associated with the appearance of a crust on bread and fried potatoes, as well as the formation of a dense film on maleic underwear under the influence of a hot iron.

Another polysaccharide known to you - cellulose - can also be hydrolyzed to glucose during prolonged heating with mineral acids. The process is slow, but brief. This process underlies many hydrolysis industries. They serve to obtain food, feed and technical products from non-food plant raw materials - waste from logging, woodworking (sawdust, shavings, wood chips), processing of crops (straw, seed husks, corn cobs, etc.).

The technical products of such industries are glycerin, ethylene glycol. organic acids, fodder yeast, ethyl snirt, sorbitol (hexahydric alcohol).

Protein hydrolysis

Hydrolysis can be suppressed (significantly reduce the amount of salt undergoing hydrolysis).

a) increase the concentration of the solute
b) cool the solution;
a) introduce one of the hydrolysis products into the solution; for example, acidify the solution if it is acidic as a result of hydrolysis, or alkalinize if it is alkaline.

Significance of hydrolysis

Salt hydrolysis has both practical and biological significance.

Even in ancient times, mole was used as a detergent. The ash contains potassium carbonate, which is hydrolyzed as an anion in water, the aqueous solution becomes soapy due to the OH ions formed during hydrolysis.

At present, we use soap, washing powders and other detergents in everyday life. The main component of soap is sodium or potassium salts of higher fatty carboxylic acids: stearates, palmitates, which are hydrolyzed.

In the composition of washing powders and other detergents, salts of inorganic acids (phosphates, carbonates) are specially introduced, which enhance the washing effect by increasing the pH of the medium.

Salts that create the necessary alkaline environment of the solution are contained in a photographic developer. These are sodium carbonate, potassium carbonate, borax and other salts that hydrolyze to the anion.

If the acidity of the soil is insufficient, the plants develop a disease - chlorosis. Its signs are yellowing or whitening of the leaves, lag in growth and development. If pH> 7.5, then ammonium sulfate fertilizer is added to it, which contributes to an increase in acidity due to hydrolysis by the cation passing in the soil.

invaluable biological role hydrolysis of some salts that make up the body.

Note that in all hydrolysis reactions, the oxidation states chemical elements do not change. Redox reactions are usually not classified as hydrolysis reactions, although in this case the substance interacts with water.

What factors can affect the degree of hydrolysis

As you already know from the definition, hydrolysis is the process of decomposition with the help of water. In a solution, salts are present in the form of ions and their driving force, which provokes such a reaction, is called the formation of low-dissociating particles. This phenomenon is characteristic of many reactions occurring in solutions.

But not always ions, interacting with water, create low-dissociating particles. So, as you already know that salt is made up of a cation and an anion, then such types of hydrolysis are possible as:

In the case of the entry of the reaction of water with a cation, we get hydrolysis by the cation;
If, however, the reaction of water occurs only with the anion, then we obtain hydrolysis by the anion;
With the simultaneous entry of a cation and anion into a reaction with water, we obtain joint hydrolysis.

Because we already know that hydrolysis has a reversible reaction, then some factors affect its equilibrium state, which include: temperature, concentration of hydrolysis products, concentrations of reaction participants, additions of foreign substances. But, when gaseous substances do not take part in the reaction, then these substances do not affect the pressure, with the exception of water, since its concentration is constant.

Now consider examples of expressions for hydrolysis constants:

Temperature can be a factor that affects the equilibrium state of hydrolysis. Thus, with an increase in temperature, the equilibrium of the system shifts to the right, and in this case, the degree of hydrolysis increases.

If we follow the principles of Le Chatelier, then we see that with an increase in the concentration of hydrogen ions, the equilibrium shifts to the left, while the degree of hydrolysis decreases, and with an increase in concentration, we see the effect for the reaction in the second formula.

With the concentration of salts, we can observe that the equilibrium in the system shifts to the right, however, in this case, the degree of hydrolysis, if we follow the principles of Le Chatelier, decreases. If we consider this process from the point of view of a constant, we will see that with the addition of phosphate ions, the equilibrium will shift to the right and their concentration will increase. That is, to double the concentration of hydroxide ions, it is necessary to increase the concentration of phosphate ions by four times, although the value of the constant should not change. It follows from this that the ratio
will decrease by 2 times.

With the dilution factor, there is a simultaneous decrease in the particles that are in solution, except for water. If we follow the principle of Le Chatelier, then we see that the equilibrium is shifted and the number of particles increases. But such a hydrolysis reaction occurs without taking into account water. In this case, the dilution of the equilibrium shifts in the direction of the course of this reaction, that is, to the right, and it is natural that the degree of hydrolysis will increase.

The equilibrium position can be influenced by the addition of foreign substances, provided that they react with one of the participants in the reaction. For example, if we add a solution of sodium hydroxide to a solution of copper sulfate, then in this case the hydroxide ions present in it will begin to interact with hydrogen ions. In this case, it follows from the Le Chatelier principle that, as a result, the concentration will decrease, the equilibrium will shift to the right, and the degree of hydrolysis will increase. Well, when sodium sulfide is added to the solution, the equilibrium will shift to the left, due to the binding of copper ions to the practically insoluble copper sulfide.

Let's sum up from the material studied and come to the conclusion that the topic of hydrolysis is not complicated, but it is necessary to clearly understand what hydrolysis is, have a general understanding of the shift in chemical equilibrium and remember the algorithm for writing equations.

Tasks

1. Select examples of organic substances undergoing hydrolysis:
glucose, ethanol, bromomethane, methanal, sucrose, formic acid methyl ester, stearic acid, 2-methyl butane.

Make equations for hydrolysis reactions; in the case of reversible hydrolysis, indicate the conditions that allow shifting the chemical equilibrium towards the formation of the reaction product.

2. Which salts undergo hydrolysis? What kind of environment can have in this case aqueous solutions of salts? Give examples.

3. Which of the salts undergo cation hydrolysis? Make equations for their hydrolysis, indicate the environment.

The reaction of metabolic decomposition of substances with water is called hydrolysis. Inorganic and organic substances - salts, carbohydrates, haloalkanes, proteins, esters - are exposed to such influence. The process is reversible and irreversible.

inorganic substances

Among inorganic compounds, soluble mineral salts undergo hydrolysis due to the interaction of ions with water molecules. As a result, the salt decomposes into cations and anions, that is, an electrolyte is formed.

Rice. 1. Classification of salts by solubility.

Salts can be formed:

weak acid and strong base (Na 2 CO 3);
strong acid and weak base (ZnSO 4);
weak acid and weak base (Fe 2 (CO 3) 3);
strong acid and strong base (Na 2 SO 4).

Salt ions during hydrolysis are able to form weak electrolytes with H + and OH. Depending on the connection with water ions, reactions proceeding along the cation or anion, as well as along the cation and anion, are distinguished.

Salts consisting of a strong acid and a strong base do not undergo hydrolysis.

The description of the process for different salts is presented in the table.

*Hydrolysis*	*Salt*	*Description*
By anion	Weak acid, strong base	It flows in steps. A weakly alkaline environment is formed. The reaction is reversible. Salt anions bind to water cation: 1. Na 2 CO 3 + H 2 O ↔ NaHCO 3 + NaOH; 2. NaHCO 3 + HOH ↔ H 2 CO 3 + NaOH
By cation	Strong acid, weak base	It proceeds in steps, in the second and third stages - slightly. A slightly acidic environment is formed. The reaction is reversible. Salt cations bind to water anions: NH 4 Cl + H 2 O ↔ NH 4 OH + HCl
By anion and cation	Weak acid, weak base	It flows completely. Equilibrium shift towards end products. The medium depends on the dissociation constants. The reaction is irreversible: Al 2 S 3 + 6H 2 O → 2Al(OH) 3 ↓ + 3H 2 S

Rice. 2. Scheme of salt hydrolysis.

A reversible process obeys Le Chatelier's principle: the reaction rate increases when water is added (solution is diluted) or the temperature rises.

organic matter

High-molecular substances are exposed to water decomposition. As a result of hydrolysis, monomers are formed or the bonds between carbon and substituents are broken. Additional conditions are necessary for the reaction to take place.

A brief description of the decomposition by water of organic substances is described in the table.

*Substance*	*Description*	*The equation*
haloalkanes	Occurs in an alkaline environment. Alcohols are formed	C 5 H 11 Cl + H 2 O (NaOH) → C 5 H 11 OH
Esters	Formation of carboxylic acids and alcohols	CH 3 COOCH 3 + H 2 O ↔ CH 3 COOH + CH 3 OH
alcoholates	Alcohol and alkali are formed	C 2 H 5 ONa + H 2 O ↔ C 2 H 5 OH + NaOH
Carbohydrates	Oligosaccharides and polysaccharides are exposed. Monosaccharides are formed	C 12 H 22 O 11 (sucrose) + H 2 O → C 6 H 12 O 6 (glucose) + C 6 H 12 O 6 (fructose)
	Partially decomposed. Amino acids are formed	CH 2 (NH 2) -CO-NH-CH 2 -COOH + H 2 O ↔ 2CH 2 (NH 2) -COOH
	Occurs when heated under the action of acids and alkalis. Glycerol and salts of carboxylic acids are formed	(C 17 H 35 COO) 3 C 3 H 5 + H 2 O → C 3 H 8 O 3 + 3C 17 H 35 COONa

Nucleic acids are hydrolyzed in stages. Initially, nucleotides are formed, which also undergo hydrolysis. End products - monosaccharides and phosphoric acid

Rice. 3. Scheme of hydrolysis of nucleic acids.

What have we learned?

From the topic of the 11th grade chemistry lesson, we learned that hydrolysis is the process of decomposition of substances under the action of water. Salts, esters, haloalkanes, alcoholates, proteins, fats, carbohydrates undergo reactions. The process often proceeds in stages. Depending on the final products, hydrolysis proceeds reversibly and irreversibly. The interaction of substances with water can be accelerated and complete decomposition can be achieved by adding water or raising the temperature.

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1 HYDROLYSIS OF ORGANIC AND INORGANIC SUBSTANCES

2 Hydrolysis (from the ancient Greek "ὕδωρ" water and "λύσις" decomposition) one of the types chemical reactions where, when substances interact with water, the initial substance decomposes with the formation of new compounds. The mechanism of hydrolysis of compounds of various classes: - salts, carbohydrates, fats, esters, etc. has significant differences

3 Hydrolysis of organic substances Living organisms carry out the hydrolysis of various organic substances in the course of reactions with the participation of ENZYMES. For example, during hydrolysis, with the participation of digestive enzymes, PROTEINS are broken down into AMINO ACIDS, FATS into GLYCEROL and FATTY ACIDS, POLYSACCHARIDES (for example, starch and cellulose) into MONOSACCHARIDES (for example, into GLUCOSE), NUCLEIC ACIDS into free NUCLEOTIDES. When fats are hydrolyzed in the presence of alkalis, soap is obtained; hydrolysis of fats in the presence of catalysts is used to obtain glycerol and fatty acids. Ethanol is obtained by hydrolysis of wood, and peat hydrolysis products are used in the production of fodder yeast, wax, fertilizers, etc.

4 1. Hydrolysis of organic compounds fats are hydrolyzed to obtain glycerol and carboxylic acids (saponification with NaOH):

5 starch and cellulose are hydrolyzed to glucose:

7 TEST 1. During the hydrolysis of fats, 1) alcohols and mineral acids 2) aldehydes and carboxylic acids 3) monohydric alcohols and carboxylic acids 4) glycerol and carboxylic acids ANSWER: 4 2. Hydrolysis undergoes: 1) Acetylene 2) Cellulose 3) Ethanol 4) Methane ANSWER: 2 3. Hydrolysis undergoes: 1) Glucose 2) Glycerin 3) Fat 4) Acetic acid ANSWER: 3

8 4. During the hydrolysis of esters, the following are formed: 1) Alcohols and aldehydes 2) Carboxylic acids and glucose 3) Starch and glucose 4) Alcohols and carboxylic acids ANSWER: 4 5. Starch hydrolysis produces: 1) Sucrose 2) Fructose 3) Maltose 4) Glucose ANSWER: 4

9 2. Reversible and irreversible hydrolysis Almost all the considered reactions of hydrolysis of organic substances are reversible. But there is also irreversible hydrolysis. General property irreversible hydrolysis - one (preferably both) of the hydrolysis products must be removed from the reaction sphere in the form of: - SEDIMENT, - GAS. CaC₂ + 2H₂O = Ca(OH)₂ + C₂H₂ During the hydrolysis of salts: Al₄C₃ + 12 H₂O = 4 Al(OH)₃ + 3CH₄ Al₂S₃ + 6 H₂O CaH₂ + 2 H₂O = 2 Al(OH)₃ + 3 H₂S = 2Ca(OH )₂ + H₂

10 HYDROLYSIS SOLEY Hydrolysis of salts is a kind of hydrolysis reactions caused by the occurrence of ion exchange reactions in solutions of (aqueous) soluble electrolyte salts. driving force process is the interaction of ions with water, leading to the formation of a weak electrolyte in ionic or molecular form (“ion binding”). Distinguish between reversible and irreversible hydrolysis of salts. 1. Hydrolysis of a salt of a weak acid and a strong base (anion hydrolysis). 2. Hydrolysis of a salt of a strong acid and a weak base (cation hydrolysis). 3. Hydrolysis of the salt of a weak acid and a weak base (irreversible) The salt of a strong acid and a strong base does not undergo hydrolysis

12 1. Hydrolysis of a salt of a weak acid and a strong base (anion hydrolysis): (solution has an alkaline environment, the reaction is reversible, hydrolysis in the second stage proceeds to an insignificant degree) 2. Hydrolysis of a salt of a strong acid and a weak base (cation hydrolysis): (the solution has an acidic environment, the reaction proceeds reversibly, hydrolysis in the second stage proceeds to an insignificant degree)

13 3. Hydrolysis of a salt of a weak acid and a weak base: (the equilibrium is shifted towards the products, the hydrolysis proceeds almost completely, since both reaction products leave the reaction zone in the form of a precipitate or gas). The salt of a strong acid and a strong base does not undergo hydrolysis and the solution is neutral.

14 SCHEME OF SODIUM CARBONATE HYDROLYSIS NaOH strong base Na₂CO₃ H₂CO₃ weak acid > [H]+ BASIC MEDIUM ACID SALT, ANION hydrolysis

15 First hydrolysis stage Na₂CO₃ + H₂O NaOH + NaHCO₃ 2Na+ + CO₃ ² + H₂O Na+ + OH + Na+ + HCO₃ CO₃ ² + H₂O OH + HCO₃ Second hydrolysis stage NaHCO₃ + H₂O = NaOH + H₂CO ₃ CO₂ H₂O Na+ = Na₂O + HCO + OH + CO₂ + H₂O HCO₃ + H₂O = OH + CO₂ + H₂O

16 COPPER(II) CHLORIDE HYDROLYSIS SCHEME Cu(OH)₂ weak base CuCl₂ HCl strong acid< [ H ]+ КИСЛАЯ СРЕДА СОЛЬ ОСНОВНАЯ, гидролиз по КАТИОНУ

17 First stage of hydrolysis CuCl₂ + H₂O (CuOH)Cl + HCl Cu+² + 2 Cl + H₂O (CuOH)+ + Cl + H+ + Cl Cu+² + H₂O (CuOH)+ + H+ Second stage of hydrolysis (СuOH)Cl + H₂O Cu(OH)₂ + HCl (Cu OH)+ + Cl + H₂O Cu(OH)₂ + H+ + Cl (CuOH)+ + H₂O Cu(OH)₂ + H+

18 ALUMINUM SULFIDE HYDROLYSIS SCHEME Al₂S₃ Al(OH)₃ H₂S weak base weak acid = [H]+ NEUTRAL REACTION OF THE MEDIUM irreversible hydrolysis

19 Al₂S₃ + 6 H₂O = 2Al(OH)₃ + 3H₂S HYDROLYSIS OF SODIUM CHLORIDE NaCl NaOH HCl strong base strong acid = [H]+ NEUTRAL REACTION OF THE ENVIRONMENT no hydrolysis occurs NaCl + H₂O = NaOH + HCl Na+ + Cl + H₂O = Na+ + OH + H+ + Cl

20 Conversion earth's crust Providing a slightly alkaline environment sea water THE ROLE OF HYDROLYSIS IN HUMAN LIFE Laundry Washing dishes Washing with soap Digestion processes

21 Write the hydrolysis equations: A) K₂S B) FeCl₂ C) (NH₄)₂S D) BaI₂ K₂S: KOH is a strong base H₂S weak acid HS + K+ + OH S² + H₂O HS + OH FeCl₂ : Fe(OH)₂ - weak base HCL - strong acid FeOH)+ + Cl + H+ + Cl Fe +² + H₂O (FeOH)+ + H+

22 (NH₄)₂S: NH₄OH - weak base; H₂S - weak acid HI - strong acid HYDROLYSIS NO

23 Perform on a piece of paper. Hand in your work to the teacher at the next lesson.

25 7. An aqueous solution of which of the salts has a neutral environment? a) Al(NO₃)₃ b) ZnCl₂ c) BaCl₂ d) Fe(NO₃)₂ 8. In which solution will the color of litmus be blue? a) Fe₂(SO₄)₃ b) K₂S c) CuCl₂ d) (NH₄)₂SO₄

26 9. Hydrolysis is not subject to 1) potassium carbonate 2) ethane 3) zinc chloride 4) fat 10. During the hydrolysis of fiber (starch), the following can be formed: 1) glucose 2) only sucrose 3) only fructose 4) carbon dioxide and water 11. Solution medium as a result of hydrolysis of sodium carbonate 1) alkaline 2) strongly acidic 3) acidic 4) neutral 12. Hydrolysis undergoes 1) CH 3 COOK 2) KCI 3) CaCO 3 4) Na 2 SO 4

27 13. Hydrolysis is not subjected to 1) ferrous sulfate 2) alcohols 3) ammonium chloride 4) esters

28 PROBLEM Explain why when pouring solutions - FeCl₃ and Na₂CO₃ - precipitates and gas is released? 2FeCl₃ + 3Na₂CO₃ + 3H₂O = 2Fe(OH)₃ + 6NaCl + 3CO₂

29 Fe+³ + H₂O (FeOH)+² + H+ CO₃ ² + H₂O HCO₃ + OH CO₂ + H₂O Fe(OH)₃

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