Intramolecular aldol condensation. asked Jun 27, 2019 in Chemistry by Anshu Priya (25.

Intramolecular aldol condensation Aldol Condensation. For an intramolecular aldol condensation to occur an alpha-hydrogen one of the methyl groups would have to be removed which would be difficult. Open in a new tab. Aldehydes and ketones can isomerize into enolates or enols under basic or acidic conditions, respectively. A. Intramolecular Aldol Condensation. The equivalent intermolecular reaction is the Claisen condensation. 6. If these rings may be produced by two The reaction begins with a Michael reaction, followed by an intramolecular aldol condensation to give a new six-membered ring containing an alpha, beta unsaturated ketone. For similar reasons, intramolecular aldol reactions of 1,5-diketones lead only to cyclohexenone products rather than to the more strained acylcyclobutenes. Aldol condensation reaction is a method to form C–C bond and reduce the O/C ratio in the molecule. When the alpha carbon of one group attacks the other, the molecule attacks itself forming a ring structure. The aldol reaction or aldol condensation, is one of the most important C-C bond formation reactions for aldehydes and ketones. Called the Dieckmann cyclization , this reaction works best on 1,6-diesters and 1,7-diesters. Claisen Condensation. 3. In aldol condensation, i-Pr-substituted bimorpholine is the most stereoselective Mixtures of aldehydes, ketones, or both, can be used in a mixed aldol condensation. Selecting the correct set involves analyzing the carbonyl reactivity’s along with the possible ring sizes of the products. b) Cross Aldol Condensation. Internal aldol condensations can occur in compounds containing two suitable carbonyl groups. One very common and important type of reaction that deals with the alpha-position of carbonyl compounds is known as aldol condensation. Steven Farmer (Sonoma State University) 22. Q8. In addition to the new C–C bond, a C-H bond has broken, as has a C–O (pi) bond: This reaction has co Intramolecular aldol reaction. Problem 23-10 Watch Intramolecular Aldol Condensation in English from Chemical Properties of Aldehydes and Ketones here. The mechanism involves nucleophilic addition, where the enolate attacks the electrophile, leading to a tetrahedral intermediate. Contributors. However, the aldol reaction is not formally a condensation reaction because it does not involve the loss of a small molecule. One such application is Intramolecular Aldol Condensation. Tcm F2 cyclase represents the first discrete enzyme for carbon-carbon bond formation via an intramolecular aldol condensation-dehydration mechanism, a key biochemical operation proposed in the early steps of the biosynthesis of all ALDOL CONDENSATION: An aldol condensation is an organic reaction in which an enol or an enolate ion reacts with a carbonyl compound to form a β‐ hydroxyaldehyde or β‐hydroxyketone, followed by a dehydration to give a conjugated enone. 2) 23. This type of reaction is often used in the synthesis of complex organic molecules, such as pharmaceuticals and agrochemicals. Reaction of compounds 6 with LHMDS at low temperature gave a single diastereomer of fused Improvement of boehmite (AlOOH)-derived aluminum oxide catalyzed intramolecular aldol condensation of 2,5-hexanedione (HDN) to 3-methyl-2-cyclopentenone (MCP) is examined by addition of another element (M: Ca, Cr, Mn, Fe, Co, Ni, Cu, Zn, Ga, Sr, In, La, Ce, Gd, and none) as 3 wt% (in theory) with thermal treatment at 600 °C. We now conclude that the rate-limiting step in the base-catalyzed aldol condensation of benzaldehydes with acetophenones, to produce chalcones, is the final loss of hydroxide and formation of the C═C How to determine the product of an intramolecular aldol condensation. Synthesis of sorbic acid that acts as a food preservative. identify the enone products from the aldol condensation of a given aldehyde or ketone. Conjugated enones, like conjugated dienes, have more inherent stability compared with their non‑conjugated counterparts. Treatment of a 1,3-diketone such We will discuss aldol condensation under acidic conditions, explore it under basic conditions, examine the mixed aldol condensation separately, and finally, I will provide a dedicated tutorial with examples and a nifty trick that will allow you Intramolecular Aldol condensations happen when a single molecule contains 2 reaction aldehyde/ketone groups. 0 Aldol Condensation Reaction Requirements The aldehyde or ketone involved must have at least one α-hydrogen (hydrogen attached to the carbon adjacent to the carbonyl group). 8 Intramolecular Aldol Condensation. 73 For example, base-catalyzed conjugate addition of (301a,b; equation 67) followed by intramolecular aldol condensation affords the hydrindenones (302a,b) in high yields with excellent stereoselectivity Learn about aldol condensation in organic chemistry through Khan Academy's engaging video tutorial. Convergent Synthesis of Enantioenriched ortho-Fused Tricyclic Diketones via Catalytic Asymmetric Intramolecular Vinylogous Aldol Condensation. The presence of a cyclic, six-membered α, β-unsaturated ketone in a target molecule suggest that a Robinson Annulation may be utilized in its synthesis. The second part of the Robinson Annulation is the intramolecular aldol condensation. The mechanism of the Dieckmann cyclization, shown in Figure \(\PageIndex{1}\), is the same as that of the Claisen condensation. 4: Intramolecular Aldol Reactions is shared under a CC BY-NC-SA 4. About. Conclusions and outlook. 1. The enolates or enols can further add to the carbonyl group in aldehydes or ketones, giving β-hydroxyl carbonyl Lab 9: Aldol Condensation Jeremy Sanders November 4, 2024 CHEM 2212L Introduction This lab is focused on the process of aldol condensation, a base-catalyzed coupling of two aldehydes or ketones. The aldol reaction involves the addition of the enolate (or equivalent functional group) of one carbonyl-containing compound (aldehyde or ketone) to a second carbonyl-containing compound (aldehyde or ketone) to Intramolecular Aldol Condensation Reaction organic chemistry tutorial video. The overall thermodynamics are similar for cyclization of 2,5-hexanedione and 2,6-heptanedione; conversion of 2,5 Because esters commonly contain both α-hydrogens and a carbonyl bond, they can undergo a reversible condensation similar to the aldol reaction called a Claisen Condensation. In summary What is Aldol Condensation? Aldol condensation occurs in aldehydes having α-hydrogen with a dilute base to give β-hydroxy aldehydes called aldols. Actually Pd enolates undergo intramolecular aldol condensation and Michael addition. 3. Study Notes. 1 answer. The resulting product, a “beta-hydroxy aldehyde” contains both an aldehyde and an alcohol. Soc. Problem 23-9 Treatment of a 1,3-diketone such as 2,4-pentanedione with base does not give an aldol condensation product. It then introduces carbon-carbon bond formation using enolate ions as nucleophiles Aldol condensation is a key reaction where an enolate ion, formed from a ketone or aldehyde, reacts with another carbonyl compound to produce a beta hydroxy carbonyl, known as an aldol. asked Jun 27, 2019 in Chemistry by Anshu Priya (25. Aldol Condensation Practice Questions. The key bond cleavages are the C=C bond of the α, β-unsaturated ketone and the The mechanistic of aldol condensation on Beta zeolites have been the subject of extensive research [3, 24, 25, 38]. You may wish to review Sections 2. In most cases two sets of If a compound has two carbonyl groups (dicarbonyl compound), it undergoes an intramolecular aldol reaction if a five- or six-membered ring can be formed: For similar reasons, intramolecular aldol reactions of 1,5-diketones lead only to cyclohexenone products rather than to the more strained acylcyclobutenes. Selecting the correct set involves analyzing the carbonyl reactivity’s along with the possible ring sizes of the 3. promoted intramolecular aldol condensation of two partiall y protected l-lyxo-hexos-5-ulose derivatives ( 39 and 40 ), in turn obtained starting from methyl β -D-galactopyranoside, takes place 22. In an "aldol addition" reaction, an enol or more commonly the more nucleophilic enolate of an aldehyde or ketone reacts with a second aldehyde or ketone forming a new carbon-carbon bond. Prof. 2 This laboratory activity on the “aldol condensation reaction” involves both of these aspects of aldehyde and ketone reactivity. 3 (drawn in grey), the self-condensation of acetone should also be considered as side reactions, Rate and equilibrium constants have been determined for both the aldol addition and the elimination steps in the intramolecular condensation reactions of 2,5-hexanedione, 2,6-heptanedione, 1-phenyl-1,5-hexanedione, and 5-oxohexanal. Self-Aldol, Crossed Aldol, Intramolecular Aldol 2. Aldol Condensation: the dehydration of Aldol products to synthesize α, β unsaturated carbonyl (enones) Intramolecular aldol reaction. This intermediate can spontaneously dehydrate to form a stable The intramolecular aldol condensation of 2,5-HD has been reported to generate 3-methyl-2-cyclopentenone (MCP) (Scheme 1), an important chemical for fuel additives [16], [17]. Cyclization occurs if the α carbon atom and the second carbonyl carbon atom can bond to form a five- or six-membered ring. This is the same as a regular aldol condensation, just with two ketones on the same molecule. Example of Intramolecular Aldol Condensation. Organic Letters 2022, 24 (49) , Interfacial Control of It is found that the enolization of the diketone is a key step in acid-catalyzed mechanism and the cyclization step bears a very small activation energy. The aldol condensation begins with deprotonation of the 1,5-diketone to give an enolate on C-1 [Note that there are two enolates that could be formed, on C-1 and C-3 (since the molecule is symmetrical, these are equivalent to C-7 and C-5, respectively). 1) 2,4-Pentanedione like other 1,3-Diketones have particularly acidic alpha-hydrogens between the two carbonyl. (See post: The Aldol Addition and Condensation) Enols can also perform the aldol reaction aldehydes and ketones, if an acid Intramolecular aldol reactions (when the enolate anion and the carbonyl acceptor are in the same molecule) are most successful for formation of five- and six- reaction can undergo an intramolecular aldol condensation to form a six-membered ring. 1k points) class-12; aldehydes-and-ketones; 0 votes. Understand the product formation in cross aldol condensation. In a fashion similar to the aldol reaction, one ester acts as a Claisen enolate donor (nucleophile) while a second ester acts as the Claisen acceptor (electrophile). In a typical aldol condensation, either an enolate (under basic conditions) or an enol (under acidic conditions) will act as a nucleophile and react Aldol condensation has been considered as a key reaction in biomass valorization due to its promising route to various value-added chemicals [5]. Revisiting Intramolecular Reactions; The Aldol Condensation; The Intramolecular Aldol Condensation Worked Example. this method allows you to quickly and confidently predict Intramolecular aldol reactions (when the enolate anion and the carbonyl acceptor are in the same molecule) are most successful for formation of five- and six- reaction can undergo an intramolecular aldol condensation to form a six-membered ring. Intramolecular aldol condensation reactions are also very common and do form stable aldol product as long as the ring chain contains at least five carbons. 2. Typically under basic conditions, the aldol product is usually the final product while under acidic conditions, the aldol carbonyl can go on to form the alpha,beta-unsaturated product. Please draw the expected product of an intramolecular aldol condensation with the following molecule: Answer. The properties of the catalysts can be tuned either by the selection of an appropriate acid for the salt formation or by the change of a substituent at the nitrogen atom. identify the product formed when a given dicarbonyl compound undergoes an intramolecular aldol condensation. CONCLUSIONS With all the polyketonic substrates studied it was found, in agreement with our predictions based on stereoelectronic considerations, that intramolecular aldol condensation via a favored 6-(enolendo)-exo-trig ring closure predominated to the exclusion of the disfavored 5(enolendo)-exo-trig process, and also to the exclusion of all Comprehend the mechanism of aldol condensation in base and acid medium. Introduction. Created by Jay. The Dieckmann Condensation (or intramolecular Claisen condensation) If the nucleophile and electrophile of the Claisen condensation are joined together, the reaction is a cyclization and is known as the Dieckmann Houk and coworkers have theoretically studied the stereoselectivity of proline-catalyzed asymmetric inter- and intramolecular aldol reactions successively [9, 10], Besides cyclization and decarboxylation depicted in Fig. 1]undec-7-en-9-one (2) has been synthesized via intramolecular aldol condensation of the precursor 3 by combined use of lithium diisopropylamide (LDA) and CeCl 3. Predict the major product in intramolecular aldol condensation. Lewis et al. One of the two ester groups is converted into an The name aldol condensation is also commonly used, especially in biochemistry, to refer to just the first (addition) stage of the process—the aldol reaction itself—as catalyzed by aldolases. Intramolecular aldol The Dieckmann condensation is the intramolecular chemical reaction of diesters with base to give β-ketoesters. a) Aldol condensation: This occurs when two molecules of aldehydes The syntheses of 2,2′-spirobi[indene] derivatives based on a gold(I)-catalyzed tandem strategy involving intramolecular methoxylation/double aldol condensation were achieved. 1 Proline Catalysed Intramolecular Aldol Condensation The first report of a direct asymmetric aldol reaction catalyzed by a small molecule was the Hajos-Parrish- Eder-Sauer-Wiechert Aldol Condensation: the dehydration of aldol products to synthesize α, β unsaturated carbonyls (enones) Intramolecular aldol reaction. org/science/organic- Intramolecular Aldol Condensation. As with most ring forming reaction five and six membered rings are preferred. Describe and illustrate. During this Monosalts of N-substituted bimorpholine derivatives are efficient organocatalysts in intramolecular and intermolecular aldol reactions. The Acid-Catalyzed Aldol Reaction And Its Three Paths For Acid-Catalysis. When an aldehyde group is present in the allyl fi-keto ester 738, intramolecular aldol condensation takes place yielding the cyclic aldol 739 as a main product[463]. identify the dicarbonyl compound which, when treated with a suitable base, could be used to prepare a Intramolecular aldol condensation is a tricky topic. write an equation to illustrate an intramolecular aldol reaction. Stork reported excellent stereochemical control in the intramolecular Michael addition to produce methyl-substituted cyclopentane systems. The detailed kinetics and equilibrium for the intramolecular aldol condensation reaction of 2,5-hexanedione, 2, 6-heptanedione, 1-phenyl-1, 5-hexanedione and 5-oxohexanal were studied and correlated in terms of Marcus theory. The reaction can occur between two identical carbonyl compounds (symmetrical aldol) or two different carbonyl compounds (asymmetrical aldol). Previously we saw how the conjugate base of enols (known as “enolates“) can add to aldehydes and ketones, a reaction known as the aldol reaction. What is the product? There are 4 possibilities because the reaction mixture contains the two Diastereoselective intramolecular aldol condensations are investigated in an experimental and computational study of 1,6-diketones. Several industrial reactions are also summarized, including the Aldox process, Perkin reaction, and Meerwein-Ponndorf-Verley reaction. At the same time, the diketone 740 is formed as a minor product by /3-eIimination. 2 on dienes, which gives a molecular orbital description showing π electron distribution http://leah4sci. 10 Mixed Aldol Condensations. Problem 23-9. MCAT For similar reasons, intramolecular aldol reactions of 1,5-diketones lead only to cyclohexenone products rather than to the more strained acylcyclobutenes. Problem 23-10. Intramolecular aldol condensation reactions. Charles Adolphe Wurtz Intramolecular aldol reaction. As with other aldol reaction the addition of heat causes an aldol condensation to occur. Cyclization occurs if the α carbon atom and the Intramolecular Aldol Condensation. Treatment of a 1,3-diketone such as 2,4-pentanedione with base does not give an aldol condensation product. When a compound has two carbonyl groups, it can undergo intramolecular aldol condensation in the presence of dilute base (if a-H atoms are present in the compound). Intramolecular aldol condensations are more favorable than intermolecular aldol condensations. Learn my quick shortcut followed by the step by step mechanism for completing an internal or intramolecular aldol condensation reaction. Although aldol condensation is one of the most important organic reactions, capable of forming new C–C bonds, its mechanism has never been fully established. First, a base must be added to 5. An intramolecular reaction is readily The total number of intramolecular aldol condensation products formed form Y is. Wurtz, C. All the reactions, with the readily explained exception of the intramolecular aldol addition of 5 Aldol condensation occurs when an aldehyde contains an ɑ–hydrogen atom. 1872, 17, 436 442. In the scheme given below, the total number of intramolecular aldol condensation products formed from ‘y’ is. com/enolate presents: Intramolecular aldol condensation reaction trick, mechanism, and product to reactantsNeed help with orgo? Download my f Intramolecular Claisen condensations can be carried out with diesters, just as intramolecular aldol condensations can be carried out with diketones (Section 23. Watch all CBSE Class 5 to 12 Video Lectures here. Aldol‑like condensations can be brought about between aldehydes and a variety of compounds containing acidic alpha‑hydrogen atoms, including diethyl malonate, acetic Aldehydes and ketones with an α hydrogen atom undergo a base-catalyzed carbonyl condensation reaction called the aldol reaction. Introduction In organic synthesis, by far the most important activating groups are the carbonyl and carboxylic ester groups. Nuclear magnetic resonance studies suggest the ability to tune both isomerization directions upon irradiation with different ultraviolet and visible light (370–640 nm light-emitting diode). The reaction for the same is Formation of cyclic compounds by intramolecular aldol condensation. Analysis: 6-Oxoheptanal has three unique sets of alpha-hydrogens which could be deprotonated to form an enolate. Ab initio results show the importance of the acid medium and disapprove the Intramolecular Claisen condensations can be carried out with diesters, just as intramolecular aldol condensations can be carried out with diketones (Section 23. This Intramolecular aldol condensation of 2,5-hexanedione. For example, treatment of acetaldehyde with a base such as sodium ethoxide or sodium hydroxide in a protic solvent leads to rapid and reversible formation of 3-hydroxybutanal, known commonly as aldol ( ald ehyde The first total synthesis of albaflavenone, a novel antibiotic sesquiterpene, has been accomplished via the concise construction of its zizaene skeleton utilizing sequential intramolecular aldol condensation followed by chemo- and diastereoselective reduction of the conjugated carbon–carbon double bond. Examination of the scope of this tandem ALDOL. Diastereoselective intramolecular aldol condensations are investigated in an experimental and computational study of 1, 6-diketones. The equilibrium generally favors the condensation product in the case of aldehydes with no α substituent (RCH 2 CHO) but favors the reactant for disubstituted aldehydes (R 2 CHCHO) and for most ketones. Chim. Intramolecular aldol reaction. Intramolecular Aldol Condensation: When 2-hydroxybenzaldehyde is subjected to base catalysis, intramolecular aldol condensation Worked Example 23. Selective intramolecular aldol condensation of 2,5-hexanedione (HD), which is producible from 5-hydroxymethyl-2-furaldehyde (HMF) via hydrogenolysis and successive hydrolysis, towards 3-methyl-2 Formation of the intramolecular Aldol condensation product. a) Dieckmann condensation – An Intramolecular Claisen Reaction; Crossed Claisen and Claisen Variation Reactions; Claisen Condensation Practice Problems; Stork Enamine Synthesis; next segment of the Robinson annulation, the intramolecular aldol condensation. The combination of both experimental and computational approaches brings The aldol condensation of ketones with aryl aldehydes to form α,β-unsaturated derivatives is called the Claisen-Schmidt reaction. Skill 23. 14 Write an equation to illustrate a Claisen condensation reaction. Molecules which contain two carbonyl functionalities have the possibility of forming a ring through an intramolecular aldol reaction. It begins by outlining the learning objectives which are to understand enolate chemistry, write aldol reactions, comprehend the base and acid catalyzed mechanisms, understand cross-aldol and intramolecular aldol products. This synthetic work was completed in nine steps from Rate and equilibrium constants have been determined for both the aldol addition and the elimination steps in the intramolecular condensation reactions of 2,5-hexanedione, 2,6-heptanedione, 1-phenyl-1,5-hexanedione, and 5-oxohexanal. Some of the compounds like formaldehyde, aromatic aldehyde, trimethyl acetaldehyde, and diaryl ketones do not undergo aldol condensation reaction due to the lack of α-H atom. Missed the previous lesson? https://www. The intramolecular aldol condensation of HD to 3-methylcyclopent-2-en-1-one (MCP) (Scheme 1), in particular, is essential in producing chemicals used as gasoline additives and rocket fuels [6], [7 Exercises \(\PageIndex{1}\) 1) Briefly explain why the molecule, 2,4-pentanedione, when reacted with a base would mostly likely not produce an intramolecular aldol condensation product. This reaction can yield cinnamaldehyde as the product. Dieckmann Condensation. Retro-Aldol Challenge Mechanism. This approach involves an effective intramolecular aldol condensation to construct a bicyclic skeleton, a stereoselective rhodium-catalyzed 1,4-addition, a ring-closing metathesis, and several This document discusses the aldol condensation reaction mechanism. Explain. 0 license and was authored, remixed, and/or curated by LibreTexts. Table of Contents Intramolecular Aldol Condensation Na 2 CO 3, H 2 O heat O O O (96%) even ketones give good yields of aldol condensation products when the reaction is intramolecular . Cyclization happens when the first carbonyl carbon atom and the second carbonyl carbon atom can form a five- or six-membered ring by forming a covalent link. Palagin et al. Steric factors are probably responsible for these trends, since increased Intramolecular Aldol Condensation. a) Aldol condensation. Conventionally, basic catalysts such as NaOH and KOH can catalyze the aldol condensation of 2,5-HD to MCP [16]. Bull. An intramolecular reaction is readily The aldol condensation is the coupling of an enolate ion with a carbonyl compound to form a -hydroxycarbonyl, and sometimes, followed by dehydration Example 5, Intramolecular aldol reaction 13 Example 6, Intramolecular vinylogous aldol reaction 15 References 1. It is named after the German chemist Walter Dieckmann (1869–1925). The dicarbonyl compound 3 was prepared by allylation of 8-membered ring ketone 6b. This post goes into all the details! Table of Contents. This reaction is most commonly known as aldol condensation. 2) Draw the product of the following aldol condensation: Answers. 13 Write a detailed mechanism for the intramolecular aldol condensation. In most cases two sets of \(\alpha\) hydrogens need to be considered. Answer. 18. The exact position of the aldol equilibrium depends both on reaction conditions and on substrate structure. 7: Intramolecular Aldol Reactions is shared under a CC BY-SA 4. Limitations. Base treatment of a 1,4-diketone such as 2,5-hexanedione yields a cyclopentenone product is an example of Intramolecular aldol condensation. The intramolecular aldol condensation of 2,5-hexanedione (2,5-HD) to 3-methylcyclopent-2-enone (MCP) is an important reaction (Scheme 1) because of the important use of MCP as Intramolecular aldol condensation occurs when a molecule contains two carbonyl groups. Growth of carbon chain or intramolecular ring formation β-hydroxyaldehydes or ketones, or α,β-unsaturated aldehydes and ketones. Fr. In conclusion, these reactions are reversible and complete conversion can be achieved through excess alcohol or acetone 1-t-Butyldimethylsiloxy-8,11,11-trimethylbicyclo[5. 0 license and was authored, remixed, and/or curated by Steven Farmer, Dietmar Kennepohl, This domino reaction proceeds through aldol condensation followed by intramolecular C–S bond formation and selective cyclization in a 5-exo-trig manner. Crossed Aldol Condensation: A notable example is the crossed aldol condensation between benzaldehyde and acetone, catalyzed by a base like sodium hydroxide. studied the cross-aldol condensation of aromatic aldehydes with acetone on Hf-, Sn-, and Zr-BEA zeolites and found that the Si-O-M framework facilitated the enolization process through α-proton abstraction [10]. The intramolecular aldol condensation reaction involves the reaction of two carbonyl groups within the same molecule, resulting in the formation of a new carbon-carbon bond. If the condensation reaction occurs between two different carbonyl compounds it is called crossed aldol condensation. Planning a Synthesis Using a Robinson Annulation. If two or more reactions can yield these rings, it is necessary to consider which Worked Example. conducted an For similar reasons, intramolecular aldol reactions of 1,5-diketones lead only to cyclohexenone products rather than to the more strained acylcyclobutenes. Ab initio results show the importance of the acid medium and disapprove the possibility of a spontaneous cyclization, even for silylated compounds. 22. 6). In this tutorial I'll walk you through several examples and show you how to tackle them! When certain aldehydes are treated with strong base, two molar equivalents of the starting aldehyde may form a new C–C bond. The aldol condensation is a powerful method used for the production of various important chemicals such as 2-ethylhexanal, isophorone, mesityl oxide and crotonaldehyde [1], [2], [3]. khanacademy. Remember, aldol condensation occurs after the aldol addition and leads to ɑ, β-unsaturated carbonyl compound. Internal aldol condensations are preferable to intermolecular aldol condensations because they are more favourable. Part I. Aldol condensations are important in organic synthesis, Staüdinger cycloaddition of activated acid chlorides to 1,3-ketoaldimines, prepared in quantitative yields from 1,3-ketoaldehydes and amino esters, gave in excellent yields cis-2-azetidinones, 6−8, having the adequate functionality to obtain fused bi- and tricyclic β-lactams. oei hnv rtwlfn tuk ydatgxm lghdrhnp zasz jrwpc zpr qqnzd vdqty gztduhj zxxzk rebga mxxpia