Several functional groups OH contain molecules. Classification of compounds on functional groups

Control questions

1. What formula corresponds to fructose?

(Click the left mouse button on the selected formula)

2. What substances are formed during sucrose hydrolysis?
Answer 1: glucose and fructose
Answer 2: Starch
Answer 3: glucose and ethanol
Reply 4: Cellulose

3. Aqueous solutions Sugarrosis and glucose can be disclosed with. . .
Answer 1: Active Metal
Answer 2: Iron chloride (III)
Reply 3: sodium hydroxide
Reply 4: ammonia solution Silver oxide

4. Several functional groups -One contain molecules. . .
Answer 1: Glycerol and Phenol
Answer 2: Glycerin and glucose
Answer 3: Phenol and Formaldehyde
Answer 4: sucrose and formaldehyde

5. What is the mass of glucose, with the fermentation of which it turns out 276 g of ethanol when exiting 80%? Calculator
Reply 1: 345 g
Answer 2: 432 g
Reply 3: 540 g
Reply 4: 675 g

Test on "carboxylic acids"

1. What functional group determines the compound to the carboxylic acid class?

2. To a number of limit carboxylic acids do not belong

(CH 3) 2 CNCO

CH 3 CH 2 SNO

CH 3 PIN 3

From 17N 35 coxy

From 2N 3 coxy

3. What is the formula of the compound, if it contains 26.09% carbon, 4.35% hydrogen, 69.56% oxygen (by mass) and has a relative density of vapor vapor equal to 2,875?

4. Specify the classes of compounds having a general formula with N H 2N O 2.

simple ethers

essentials

aldehydes

carboxylic acids

double alcohols

5. Substance having a name 4,4-dimethyl gexane acid, Matches StroTPA

6. Call the connection on the Nomenclature of the Jew

7. Install the correspondence between the acid formula and its trivial name:

9. What are their reduced compounds are heptaneic acid isomers?

CH 3 -CH 2 -CH 2 (CH 3) -CH 2 -COOCH 3

CH 3 -CH (C 2 H 5) -CH 2 -O-CHO 2 -CHO

CH 3 -CH 2 -CH 2 (CH 3) -CH 2 -COOH

(CH 3) 2 CH 2 -CH 2 (CH 3) -CH 2 -COOH

10. The number of structural isomers corresponding to the formula with 4 H 9 COOH is equal

11. Spatial isomerism is possible for acids



(CH 3) 2 CH-COOH

C 2 H 5 -CH (CH 3) -COOH

HOOC-CH \u003d CH-CH 2 -COOH

HOOC-C (CH 3) 2 -COOH

CH 2 \u003d C (CH 3) -COOH

C 2 H 5 -CH \u003d CH-COOH

HOOC-CH 2 -C≡C-CH 3

12. The number of all isomers corresponding to the formula with 3 H 5 COOH is equal

13. Which of the above statements not right?

In the formic acid molecule, all atoms lie in the same plane.

Grouping O \u003d C-O in the carboxyl group forms a pairing system (delocalized communication).

Atoms of hydrogen and oxygen in the carboxyl group are capable of forming hydrogen bonds.

An electron pair of oxygen in the on-group participates in the conjugation with the group C \u003d O.

In relation to the hydrocarbon radical, the group is manifolding + i-effect.

Group -Oson lowers electron density on a hydrocarbon radical.

14. The distribution of electron density in the carboxyl group reflects the scheme

15. Specify the type of hybridization of atoms in the carboxyl group -Cooh

a) carbon;
b) oxygen in the group C \u003d O;
c) oxygen in the ON group.

a) SP 2; b) SP 2; c) SP 3

a) SP 2; b) SP 2; c) SP 2

a) SP 3; b) SP 3; c) SP 3

a) SP; b) SP 2; c) SP 2

16. The carboxyl group with respect to the hydrocarbon radical in acrylic acid CH 2 \u003d CH-SON show

+ I. -Effect

+ M. -Effect

- M. -Effect

- I. -Effect

17. What approval is wrong?

Ethanol has a lower melting point than etching acid.

The boiling point of methanic acid is higher than that of methanol.

Propaneic acid in water dissolves better than butane.

The boiling point of the etchic acid is higher than that of Bhutan.

Methanic acid under normal conditions is gas.

Acetic aldehyde boils at a lower temperature than acetic acid.

18. Of the proposed carboxylic acids, the best solubility in water has

stearinic acid

oil Acid

propionic acid

valeric acid

palmitic acid

19. Indicate which acid has the greatest degree of dissociation.

CCL 3 -CH 2 -CH 2 -COOH

CH 2 F-CH 2 -COOH

20. Install the correspondence between the general formula of the functional derivative of carboxylic acid and its name.

Rcocl
RCN.
Rcoor "
RCONH 2.
(RCO) 2 o

21. As a result of the reaction of acetic acid with propanol-1 formed

methylpropionate

propyl formate

ethyl acetate

propilacetate

ethyl formate

22. We have been published by the formula of substances. Choose those that are corresponding to amides.

23. Select reagents and conditions suitable for the following transformations:

1) NH 3; 2) heating; 3) HCN; 4) CO 2 + H 2 O

1) NH 3; 2) heating; 3) P 2 O 5, T; 4) H 2 O (H +)

1) NH 4 Oh; 2) HCl; 3) PCL 5; 4) H 2 O (HO -)

1) NH 4 Cl; 2) NH 3; 3) NACN; 4) H 2 O (H +)

24. The main product of the reaction of benzoic acid C 6 H 5 -Con with chlorine in the presence of the Catalyst AlCl 3 is

4-chlorobenzoic acid

2,4,6-trichlorobenzoic acid

chlorobenzene.

3-chlorobenzoic acid

2,4-dichlorobenzoic acid

3-chlorobenzaldehyde

25. What is the mechanism of reactions leaking with a gap communication C-O In the carboxyl group?

electrophile connection

nucleophilic substitution

radical joining

nucleophilic joining

radical substitution

electrophile replacement

26. In one stage impossible receive

propionic acid from propanone

butanium oil

benzoic acid from benzaldehyde

acetic acid from acetaldehyde

27. Specify the substance from which directly it is impossible Get acetic acid.

CH 3 CH 2 CH 2 CH 3

28. For vegetable fats is not characteristic of the reaction

oxidation

hydrolysis

hydrogenation

esterification

29. The soaps include a substance whose formula

From 15 N 31 coxy

From 15 n 31 soups

(From 17 H 35 soo) 2 sa

From 6 H 5 comp

30. Install the correspondence between the substance and its high-quality reagent:

The Decline of the Empire, Not of the Literature (1876 - 1916)

12.1 . The era of "Thousands of Tours" in English Literature. The concept of tragic in the novels of Thomas Garde, rejection of Puritan morality. Lyrics Gardi. Social criticism in the trilogy of John Golsuorussi "Saga about Forsyites".

To the Opinion of The Present Writer, Late Victorian Literaature Is An Amazing Literary Phenomenon. ONE MIGHT. take the year 1891 AS AN EXAMPLE. That One Year Saw The Publication Of A Great Number of Outstanding Books - TESS OF THE D "Urbervilles by Thomas Hardy, THE PICTURE OF DORIAN GRAY By Oscar Wilde, THE LIGHT THAT FAILEDby Rudyard Kipling , The Quintesence Of IBSenism By George Bernard Shaw, News from Nowhere By William Morris, And A Number of Others. Each and Every of Those Books Represents a Darkct School of Writing - "Dark" Realism of Hardy, Aesthetic Writing of Wilde, New Romanticism (and Imperialism!) Of Kipling, Socialist Writing of Morris, And What Else. IT WAS A TIME OF "A Thousand Schools" in Literature, Indeed. This Richness of Ideas and Concepts Was Produced by The Development and Diversification of the Social Structure.

12.1.1. The Writer Whose Work IS Considered to Be a Bridge Between The Victorian Age and Modern Times Is Thomas Hardy (1840-1928). Hardy "S Father, A Stonemason, ApprentICED HIM Early To a Local Architect Engaged in Restoring Old Churches. In His Early Twenties, Hardy Practiced Architecture and Was Writing poetry. . HE THEN TURNED TO NOVELS AS MORE SALABLE.

Hardy Published Two Early Novels Anonymously. THE NEXT TWO, A PAIR OF BLUE EYES (1873) and Far from the Madding Crowd (1874), In His Own Name, Were Well Received. THE NOVEL IS NOT INVESTED WITH the Tracic Gloom. Of His Later Novels.

Along With. Far from the Madding Crowd, Hardy "S Best Novels Are THE RETURN OF THE NATIVE, Which Is His Most Closely Knit Narrative; THE MAYOR OF CASTERBRIDGE; TESS OF THE D "Urbervilles (1891), And. Jude The Obscure.. All Are Pervaded by A Belief in a Universe Dominated by The Determinism of the Biology of the 17th-Century Philosopher and Mathematician Sir Isaac Newton. Occasionally the Determined Fate. Of the Individual Is Altered by Chance, But The Human Will Loses When IT Challenges Necessity. Through Intense, The Fields, The Seasons, And The Weather, Wessex. Attains A Physical Presence In The Novels and Acts As A Mirror of the Psychological Conditions and The Fortunes of the Characters.

In Victorian England, Hardy Seeemed A Blasphemer, Particularly in Jude, Which Treated Sexual Attraction As a Natural Force Unopposable by Human Will. Criticism of Jude WAS SO Harsh That Hardy Announced He Was "Cured" of Writing Novels.

AT THE AGE OF 55 HARDY RETURNED TO WRITING POETRY, A FORM HE HAD PREVIOUSLY ABANDONED. Hardy "S Techniques of Rhythm and His Diction Are Especially Noteworthy On The Last Day of The 19 Th Century - At the Last End Of The Victorian Period, Virtually Sevel Days Before Queen Victoria Died in January 1901. It Characterizes Hardy "S Vision Of His Time Very Well.

The Darkling Thrush.

I LEANT UPON A COPPICE GATE

WHEN FROST WAS SPECTRE-GRAY,

And Winter's Dregs Made Desolate

The Weakening Eye Of Day.

The Tangled Bine-Stems Scored The Sky

Like Strings of Broken Lyres,

And All Mankind That Haunted Nigh

HAD SOUGHT THEIR HOUSEHOLD FIRES.

The Land's Sharp Features Seeemed to Be

The Century's Corpse Outleant,

His Crypt The Cloudy Canopy,

The Wind His Death-Lament.

THE ANCIENT PULSE OF GERM AND BIRTH

WAS SHRUNKEN HARD AND DRY,

AND EVERY SPIRIT UPON EARTH

Seeemed Fervourless AS I.

AT ONCE A VOICE AROSE AMONG

THE BLEAK TWIGS OVERHEAD

IN A FULL-HEARTED EVENSONG

Of joy illimited;

An Aged Thrush, Frail, Gaunt and Small,

In Blast-Beruffled plume,

Had Chosen Thus To Fling His Soul

Upon The Growing Gloom.

SO Little Cause for Carolings

Of Such Ecstatic Sound

Was Written ON Terrestrial Things

Afar and Nigh Around

THAT I COULD THINK THERE TREMBLED THROUGH

His Happy Good-night Air

Some Blessed Hope, Whereof He Knew

Brief characteristic of the structure of organic compounds:

  • carbon atoms form a carbon skeleton (chain), which can be open (acyclic) or closed in a ring (cyclic or carbocyclic);
  • same by molecular compositionbut different in the structural structure of the substance are called isomers;
  • compounds that differ in one group CH 2 are called homologues and form homologous rows.

Fig. 1. Examples of isomers.

In addition to carbon atoms, organic substances may contain:

  • hydrogen;
  • nitrogen;
  • oxygen;
  • sulfur;
  • phosphorus;
  • halogens;
  • metals.

Additional elements form a functional group, which determines the belonging of the substance to a specific class, causes the physical and chemical properties of the compound. Cyclic compounds containing a functional group are called heterocyclic.

Fig. 2. Examples of heterocyclic compounds.

The main names and formulas of groups are presented in the table.

Names Group

Formulas

Oxygen

Hydroxide

Carbonyl

Carboxyl

Aldehyde

Nitrogroup

Amino group

Nitrosogroup

CyanoGroup

Thiolny

Sulfoxide

Sulfonna

Sulphide

Disulfide

Molecules containing several functional groups are called polyfunctional.

Classification

In accordance with the qualitative composition (the presence of a functional group) or the number of bonds between carbon atoms, organic substances are classified into several classes. The main types of substances are presented in the table.

View

Class

Functional group

Nomenclature

Hydrocarbons

AN (Bhutan)

EN (BUTEN)

In (Butin)

Alkadien

Dien (Butadiene)

Cycloalkanes

Cyclo- (cyclobutane)

Three cyclic -s \u003d

Benzene or -ol (methylbenzene, toluene)

Amin, amino

Amino acids

amino Acid (Aminobutanic Acid)

Ol (methanol)

Aldehydes

Al (Butanal)

He (BANON)

Carboxylic acids

Obo acid (methane acid)

Selerarganic compounds

Tiol (etanalty)

Sulfoxides

Sulfoxide (diethyl sulfoxide)

Fig. 3. Classification of organic compounds.

Hydrocarbons can attach halogens, forming halogen derivatives of hydrocarbons. They are called in accordance with the attached halogen: Brometan, fluoroethane, butyl chloride, iodoform.

Reactions

Chemical reactions characteristic of organic substances are classified on two grounds:

  • by type of chemical transformation;
  • according to the mechanism of breaking covalent bonds.

The first feature includes six types of reactions:

  • replacement- new covalent bonds are formed when replacing one atom to other atoms:

    CH 4 + CL 2 → CH 3 CL + HCl;

  • attachment - when the π-communication breaks, new σ-bonds are formed:

    C 2 H 4 + Cl 2 → C 2 H 4 Cl 2;

  • decomposition- new more simple substances are formed:

    CH 3 -CH 2 -CH 2 -CH 3 → CH 3 -CH 3 + CH 2 \u003d CH 2;

  • spliced- There is a separation of atoms from the source molecule while maintaining a carbon skeleton:

    C 2 H 5 OH → C 2 H 4 + H 2 O;

  • isomerization- There is a transition of atoms from one piece of molecule to another:

    CH 3 -CH 2 -CH 2 -CH 2 -CH 3 (Pentan) → CH 3 -CH (CH 3) -CH 2 -CH 3 (2-methylbutane);

  • oxidation - The degree of oxidation of carbon atoms increases:

    C -4 H 4 + 2O 2 → C +4 O 2 + 2H 2 O.

The covalent bond can occur in two ways:

  • freeradical- every atom in the reaction is obtained by one electron (polar covalent bonds are subjected);
  • ionic- With a reaction, the overall pair of electrons remains in one atom (undergoes are subjected to non-polar covalent bonds).

Organic substances - the most extensive group chemical compounds. Modern organic chemistry is known 141 million substances, although in late XIX. There were only 12 thousand substances a century.

What did we know?

Organic substances contain a carbon skeleton and a functional group defining the properties of the compounds. The functional group can be nitrogen, oxygen, sulfur, phosphorus. The classification of substances depends on the presence in the structure of a particular atom. Organic compounds include groups of hydrocarbons, nitrogen, oxygen-containing, seleraban substances. For organic compounds, six types of reactions are characterized by the transformation of substances and two types - to rupture a covalent bond.

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Classification of organic compounds

Organic compounds are characterized by their numerous and diversity. Therefore, their systematization is necessary. Organic compounds are classified, given the two main structural features:

The structure of the carbon chain (carbon skeleton);

The presence and structure of functional groups.

· Carbon Skeleton (Carbon Chain) - The sequence of chemically interconnected carbon atoms.

· Functional group - Atom or group of atoms that determine the belonging to a certain class and responsible for its chemical properties.

Classification of carbon chain compounds

Depending on the structure of the carbon chain, organic compounds are divided into acyclic and cyclic.

· Acyclic compounds - compounds with an open (open-on) carbon chain. These compounds are also called aliphatic.

Among the acyclic compounds distinguish limit(saturated) containing in the skeleton only single connections C-C and unforeseen (unsaturated), including multiple bonds C \u003d C and C C.

Classification of compounds on functional groups

Compounds that include only carbon and hydrogen are called hydrocarbons. Other, more numerous, organic compounds can be considered as derivatives of hydrocarbons that are formed when administered to hydrocarbons functional groupscontaining other elements. Depending on the nature of the functional groups, organic compounds are divided into classes . Some of the most characteristic functional groups and their compound classes are shown in the table:

The composition of organic compound molecules may include two or more identical or various functional groups.
For example:

HO-CH 2 -CH 2 -OH(ethylene glycol);
NH 2 -CH 2 -COOH(amino acid glycine).

All classes of organic compounds are interconnected. The transition from some compound classes to another is carried out mainly due to the transformation of functional groups without changing the carbon skeleton. The compounds of each class are a homologous series.

Homologic series - a number of related organic compounds with the same type of structure, each subsequent member of which differs from the previous on the permanent group of atoms (homologous difference).

For hydrocarbons and their derivatives, homologous difference is the methylene group -CH 2 -. For example, homologues (members of the homologous series) of limit hydrocarbons (alkanes) are methane CH 4, ethane C 2 H 6, propane from 3 H 8, etc., differing from each other to one CH 2-group:

For homologues use single methods. Homologists have close chemical properties and naturally changing physical properties.

1.3 Control questions

1. What type of organic compounds relates chloropren. (Source to obtain some varieties of synthetic rubber):

Answer 1: to unforeseen alicyclical
Answer 2: to unsteady acyclic
Answer 3: to the limit aliphatic
Answer 4: Unfoluble heterocyclic

2. Fenol functional group is. . .
Answer 1: Group -NH 2
Answer 2: Group -Cooh
Answer 3: Group -OH
Reply 4: Group -NO 2

3. Which of the above compounds are class:
a) alcohols; b) carboxylic acids?

I. C 3 H 7 Oh; II. CH 3 CHO; III. CH 3 COOH; IV. CH 3 NO 2
Answer 1: a) III; b) IV
Answer 2: a) I.; b) II.
Answer 3: a) II.; b) I.
Answer 4: a) I.; b) III

4. Build adrenaline Reflects formula

Specify the classes to which this connection can be attributed:

Reply 1: A, D, E
Answer 2: b, g, e
Answer 3: a, b, g, and
Answer 4: g, d, w
Answer 5: b, g, s

Introduction

There is a huge number of organic compounds, which, along with carbon and hydrogen, includes oxygen. An oxygen atom is contained in various functional groups that determine the accessory of the connection to a specific class.

Compounds of each class form different derivatives. For example, the derivative of alcohols includes simple ethers ROR ", to carboxylic acid derivatives - essentials Rcoor ", amides RCONH 2, anhydrida(RCO) 2 O, chloranhydrides Rcocl, etc.
In addition, the large group make up heteroofunctional compoundscontaining various functional groups:

· hydroxyaldehydes HO-R-CHO,

· hydroxyketones HO-R-CO-R ",

· hydroxy acid HO-R-COOH, etc.

The most important heterofunctional oxygen-containing compounds include carbohydrates C x (H 2 O) Y, whose molecules include hydroxyl, carbonyl and group derivatives.

To better understand the structure and properties of these compounds, it is necessary to recall the electronic structure of the oxygen atom and give the characteristics of it chemical relations with other atoms.

Alcohol

Alcohols - compounds of aliphatic series containing one or more hydroxyl groups. General formula of alcohols with one hydroxy group R-Oh..

Alcohol classification

Alcohols are classified according to various structural features.

  1. According to the number of hydroxyl groups, alcohols are divided into
  • monatomic (one group -one),
  • multiatomic (two or more groups -one).

Modern name of polyatomic alcohols - polyols (diols, triols, etc.). Examples:

  • double alcohol - ethylene glycol (ethaniol)

HO-CH 2 -CH 2 -OH

  • trehatomic alcohol - glycerin (propantriool-1,2,3)

HO-CH 2 -CH (ON) -CH 2 -OH

Double-spectacular alcohols with two-groups at one and the same carbon atom R-CH (OH) 2 unstable and, cleaving the water, immediately turn into aldehydes R-CH \u003d O. Alcohols R-C (OH) 3 do not exist.

  1. Depending on how the carbon atom (primary, secondary or tertiary) is associated with a hydroxy group, alcohols distinguish
  • primary R-CH 2 -OH,
  • secondary R 2 CH-OH,
  • tertiary R 3 C-OH.

For example:

In polyhytomic alcohols, the primary, secondary and tertincpirt groups are distinguished. For example, a throthy alcohol molecule glycerin contains two primary stained (HO-CH 2 -) and one secondary stained (-CH (OH) -) group.

  1. On the structure of radicals associated with an oxygen atom, alcohols are divided into
  • limit, or alkanolas (for example, CH 3 CH 2 -OH)
  • unforeseen, or alkeneols (CH 2 \u003d CH-CH 2 -OH)
  • aromatic (C 6 H 5 CH 2 -OH).

Unfoluble alcohols with a group with a carbon atom connected to a different double bond atom are very unstable and immediately is amazed in aldehydes or ketones. For example, vinyl alcohol CH 2 \u003d CH-OH turns into acetic Aldehyde CH 3 -CH \u003d O

Phenols

Phenols - hydroxy compound, in whose molecules of it are connected directly with the benzene core.

VRML model of phenol molecule

Depending on the number of ON groups distinguish monatomic phenols (for example, the above phenol and cresol) and multiatomic. Among the polytomic phenols are the most common ductomy:

As can be seen from the above examples, phenols are peculiar structural isomeria (Isomerization of the position of the hydroxy group).

Carbohydrates

Carbohydrates (sugar) - organic compounds having a similar structure and properties, the composition of the majority of which reflects the formula C x (H 2 O) Ywhere x, y ≥ 3.

Well-known representatives: glucose (grape sugar) From 6 H 12 o 6, sucrose (cane, beet sugar)C 12 H 22 O 11, starch and cellulose [C 6 H 10 O 5] N.

Carbohydrates are contained in the cells of plant and animal organisms and by weight constitute the bulk of the organic matter on Earth. These compounds are formed by plants in the process of photosynthesis from carbon dioxide and water with the participation of chlorophyll. Animal organisms are not able to synthesize carbohydrates and get them with vegetable food.
Photosynthesis can be viewed as a process. recovery CO 2 using solar energy. This energy is exempt in animal organisms as a result of the metabolism of carbohydrates, which is from a chemical point of view, in their oxidation.

Carbohydrates combine a variety of compounds - from low molecular weight consisting of several atoms (x \u003d 3), to polymers N with molecular weight A few million (n\u003e 10,000).
According to the number of structural units included in their molecules (the remnants of the simplest carbohydrates) and the ability to hydrolyze carbohydrates are divided into monosaccharides, oligosaccharida and polysaccharides.
Monosaccharides are not hydrolyzed with the formation of simpler carbohydrates.
Oligo and polysaccharides are split during hydrolysis to monosaccharides. Oligosaccharide molecules are contained from 2 to 10 monosaccharide residues, in polysaccharides - from 10 to 3000-5000.

Some essential carbohydrates

For most carbohydrates adopted trivial names with suffix - Iost (glucose, robose, sucrose, cellulose, etc.).

Monosaccharides

In nature, monosaccharides are the most common, in the molecules of which contain five carbon atoms (pentoses) or six (hexoses). Monosaccharides - heteroofunctional compounds, the composition of their molecules includes one carbonyl group (aldehyde or ketone) and several hydroxyl. For example:

From these formulas it follows that monosaccharides are polyhydroxyaldehydes ( aldoza, aldehydospirts) or polyhydroxyketones ( ketosis, ketoneospirts).
Ribose and glucose - aldoza (aldopentez and aldokexosis), fructose - ketosis (kethexosis).

However, not all properties of monosaccharides are consistent with such a structure. So, monosaccharides do not participate in some reactions typical of the carbonyl group. One of the hydroxy groups is characterized by an increased reactivity and its substitution (for example, on the -OR group) leads to the disappearance of the properties of aldehyde (or ketone).

Consequently, monosaccharides, in addition to the above formulas, the other structure arising from the intramolecular reaction between the carbonyl group with one of the alcohol hydroxyls is also characteristic.
IN section 3.2. The reaction of the attachment of alcohol to aldehyde to form semi-aotic R-CH (OH) OR ". Such a reaction inside one molecule is accompanied by cycling, i.e. Education cyclic semi-aotic.
It is known that 5 and 6 membrall cycles are most stable ( part II, section 3.2). Therefore, as a rule, a carbonyl group with hydroxyl is interacted at a 4th or 5th carbon atom (the numbering begins with carbonyl carbon or the end of the chain closest to it).

Thus, as a result of the interaction of the carbonyl group with one of the hydroxyl monosaccharides, there may be in two forms: open chain (oxo-form) and cyclic (semi-acetal). In the solutions of monosaccharides, these forms are in equilibrium with each other. For example, in aqueous glucose solution, the following structures exist:

Similar dynamic equilibrium structural isomers called tautomeria. This case refers to cycle Chain Tautomeria monosaccharides.

The cyclic α- and β-forms of glucose are spatial isomers, which differ in the position of the semi-acetal hydroxyl relative to the ring plane.
In α-glucose, this hydroxyl is in trance- Putting to the hydroxymethyl group -CH 2, in β-glucose - in cis- Position.

Taking into account the spatial structure of the six-membered cycle (see Animation) of the formulas of these isomers look:

Similar processes occur in solutions of ribose:

In the solid state of monosaccharides have a cyclic structure.

Chemical properties Monosaccharides are due to the presence in the molecule of functional groups of three species (carbonyl, alcohol hydroxyls and semi-acetal hydroxyl).

For example, glucose as a polyatomic alcohol forms simple and esters, comprehensive connection with copper (II) / NaOH hydroxide; As aldehyde, it is oxidized by ammonia solution of silver oxide and copper hydroxide (II), as well as bromine water, in gluconic acidCOOH- (CHOH) 4 -COOH and is restored by hydrogen into six-coat alcohol - sorbitol CH 2 OH- (CHOH) 4 -CH 2 OH; In the semi-acetal form of glucose is capable of nucleophilic replacement of semi-acetal hydroxyl on the -R group (education glycosides, oligo and polysaccharides). Similarly behave in such reactions and other monosaccharides.
The most important property of monosaccharides is their enzymatic fermentation. The decay of molecules to fragments under the action of various enzymes. Friction is mainly subjected to hexoses in the presence of enzymes allocated by yeast fungi, bacteria or mold fungi. Depending on the nature of the acting enzyme, the following types are distinguished:

Disaccharides

Disaccharides are carbohydrates whose molecules consist of two monosaccharide residues connected to each other due to the interaction of hydroxyl groups (two semi-acetal or one semi-acetal and one alcohol).
Communication connecting monosaccharide residues are called glycosida.

An example of the most common disaccharides in nature is sakhares (Beet or cane sugar). The sucrose molecule consists of glucose and fructose residues connected to each other due to the interaction of semi-acetal hydroxyls (1 → 2) -glyosidal bond:

Sakharoza, being in solution, does not enter the "silver mirror" reaction, since it is not capable of turning into an open form containing an aldehyde group. Similar disaccharides are not able to oxidize (i.e. be reducing) and are called non-establishing Sahara.

There are disaccharides, in which there are free semi-acetal hydroxyl molecules, there are equilibrium between the open and cyclic forms of molecules in aqueous solutions of such sugars. These disaccharides are easily oxidized, i.e. are restoring, for example, maltose.

In Maltose, glucose residues are connected (1 → 4) -Hlikosoidal bond.

For disaccharides characteristic hydrolysis reaction (in an acidic environment or under the action of enzymes), as a result of which monosaccharides are formed:

In hydrolysis, various disaccharides are split into the components of their monosaccharides due to the discontinuity of the relations between them ( glycosida ties):


Thus, the reaction of hydrolysis of disaccharides is the inverse process of their formation from monosaccharides.

Amino acids

Amino acids - organic bifunctional compounds, which include carboxyl groups -Oson and amino groups -NH 2.

These are substituted carboxylic acids, in whose molecules one or more hydrogen atoms of a hydrocarbon radical replaced by amino groups.

The simplest representative - Aminoacetic acid H 2 N-CH 2 -COOH ( glycine)

Amino acids classified by two structural features.

1. Differences OT mutual location Amino and carboxyl groups of amino acids are divided into α-, β-, γ-, δ-, ε-, etc.

2. According to the nature of the hydrocarbon radical, aliphatic (fat) and aromatic amino acids are distinguished. The above amino acids belong to the fat row. An example of aromatic amino acid can serve

couple-aminobensoic acid:


Disaccharides are carbohydrates whose molecules consist of two residues of monosaccharides connected to each other due to the interaction of hydroxyl groups. An example of the most common disaccharides is sucrose (beet or cane sugar). The sucrose molecule consists of glucose residues and fructose connected to each other due to the interaction of semi-acetal hydroxyls.

Sakharoza, being in solution, does not enter the "silver mirror" reaction, since it is not capable of forming an open form. Similar disaccharides are called non-establishing. Not able to oxidize.
There are disaccharides, in which there are free semi-acetal hydroxyl molecules, there are equilibrium between the open and cyclic forms of molecules in aqueous solutions of such sugars. Such disaccharides are easily oxidized, i.e. are restoring, for example, maltose.

For disaccharides, the hydrolysis reaction is characterized, as a result of which two molecules of monosaccharides are formed:

C 12 H 22 O 11 + H 2 O → 2C 6 H 12 O 6

Molecules of other oligosaccharides and polysaccharides were built by type of disaccharides

H? Polysaccharides

Control questions

1. What formula corresponds to fructose?

2. What substances are formed during sucrose hydrolysis?
Answer 1: glucose and fructose
Answer 2: Starch
Answer 3: glucose and ethanol
Reply 4: Cellulose

3. Aqueous solutions of sucrose and glucose can be distinguished by. . .
Answer 1: Active Metal
Answer 2: Bromine Water
Reply 3: sodium hydroxide
Reply 4: ammonia silver oxide solution

4. Several functional groups -One contain molecules. . .
Answer 1: Glycerol and Phenol
Answer 2: Glycerin and glucose
Answer 3: Phenol and Formaldehyde
Answer 4: sucrose and formaldehyde

5. What is the mass of glucose, with the fermentation of which it turns out 276 g of ethanol when exiting 80%?
Reply 1: 345 g
Answer 2: 432 g
Reply 3: 540 g
Reply 4: 675 g

Tasks and exercises

1. Write the equations of reactions of milk-sour and alcohol fermentation glucose. Calculate what volume of carbon oxide (IV) (N.U.) is formed when alcohol fermentation Glucose weighing 360

2. Write the equation of the reaction of the complete oxidation of glucose. Calculate carbon oxide (IV),

formed at full oxidation glucose amount of substance 2 mol.

3. What is the mass of silver oxide (I) containing 5% impurities, will go to the oxidation of glucose with the amount of substance 0.5 mol to gluconic acid?

4. How many liters of an ethyl alcohol solution (pl .,79) with a mass fraction of C2H5OH 95% will be with alcoholic fermentation glucose weighing 36 kg?

5. The mixture of glycerol, phenol and glucose weighing 36.6 g was carried out by the hydroxide of the grond (II), while the blue precipitate was formed by weight of 38 g. When the interaction of this mixture with silver oxide (I), silver was a weight of 21.6. Determine mass share Substances in the mixture.

6. Organic reactions on the mechanism of covalent bonds breaking in molecules are divided into: d) radical and ionic.

7 . If, with a covalent bond in the reacting molecules, the total electron steam is divided between atoms, particles with unpaired electrons are formed:

b) radicals;

8. Organic reactions depending on the composition of the reacting substances and reaction products are divided into reactions:

d) dissociation.

10. How many particles in the list of list (NH3, CL2, BR -, I0, H2O, Na +) refer to nucleophilic?

a) 3; b) 4; at 5; d) 6.

12. The group of atoms, determining the characteristic properties of this class of organic compounds, is called:

c) functional group;

13. The formulas of two substances CH3-CH2-OH and CH3-O-CH3 are given. These substances:

c) isomers;

14. Compounds similar to chemical properties, composition and structure, characterized by a fragment of a molecule (-CH2-), are called:

b) homologues;

Help please with the dough (!) 1 formula of the substance class of compounds a) C5H10 1) alkenes b) C4N6 2) Alkanes

C) C6H14 3) Arena 4) amines

C) C2N4O2 3) aldehydes

9. CNH2NO composition has

1) carboxylic acids and esters

2) esters and ethers

3) Easy ethers and aldehydes

4) aldehydes and ketones

10. In the propantriola molecule

Help please with the dough (!) 1 formula of substance Class of compounds a) C5H10 1) Alkens b) C4H6 2) Alkanes C) C6H14 3)

4) amines

D) C7N8 5) Alkadien 6) phenols

2. Class of compounds of the formula of substance

A) Simple ethers 1) CH3-CH (CH3) -

B) alkenes 2) CH3-CH2-O- (CH2) 4-CH3

C) aldehydes 3) CH3-CH2-C (CH3) \u003d C (CH3) -CH3

D) alcohols 4) CH3-C (CH3) -CN2-CH2-CH2-it

3. Formula of substance Class of compounds

A) C3N8O 1) unsaturated carboxylic acids

B) C4N8O 2) monatomatic alcohols

C) C2N4O2 3) aldehydes

D) C6N12O6 4) esters 5) carbohydrates

4. Compounds that include a functional group - Associate, belong to the class

1) alcohols 2) carboxylic acids 3) aldehydes 4) of ethers

5. Single bond between carbon and oxygen atoms in molecules

1) ethanol 2) acetaldehyde 3) acetylene 4) ethylene

6. The class of alkins includes a substance whose formula

1) C2N4 2) CH4 3) C2N6 4) C2N2

7. Name of hydrocarbon CH3-CH \u003d C (CH3) -CH \u003d CH2

1) 2-methylpenten-2 2) 3-methylpentadiene-1,3 3) 2-methylbutadiene 1.3 4) 3-methylbutene-1

8. The name 2-methylpenol-1 corresponds to the formula

1) But-CH2-CH2-CH (CH3) -CH2-it 2) CH3-CH (OH) -CH2-CH (CH3) -CH2-it

3) CH3-CH2-CH2-CH (CH3) -CH2-it 4) CH3-CH (CH3) -CH2-CH2-CH2-it

9. Composition CNH2NO have 1) carboxylic acids and esters

2) Esters and ethers 3) Easy ethers and aldehydes 4) aldehydes and ketones

10. In the propantriola molecule

1) 4 carbon atoms and 3 hydroxyl groups 2) 3 carbon atoms and 3 hydroxyl groups

3) 4 carbon atoms and 3 double bonds 4) 3 carbon atoms and one triple connection

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