mechanism of dehydration of alcohol class 12

How is Alkene formed from Alcohol? The rates differ for the primary, secondary and tertiary alcohols. (c) Reimer-Tiemann reaction, Question 4. Physical properties : Characteristic phenolic odour, sparingly soluble in water. Class 12 Chemistry chapter wise NCERT solution for Chemistry part 1 and Chemistry part 2 for all the chapters can be downloaded from our website and myCBSEguide mobile app for free. Download PDF's. The molecules of butane are held together by weak van der Waals’ force of attraction while those of propanol are held together by stronger intermolecular hydrogen bonding. hybridized carbon atom that follows the E1cB pathway. (ii) Nitration of anisole : Anisole reacts a mixture of concentrated sulphuric and nitric acids to yield a mixture of ortho and para nitroanisole. The subject experts have provided accurate explanations and step wise solutions for the questions provided in the textbook. (c) Reimer-Tiemann reaction Some reactive alkenes undergo direct hydration in the presence of mineral acids which act as catalysts. (b) Ethyl alcohol In alcohols, no resonance is possible hence the hydrogen atom is more firmly linked to the oxygen. Question 4. bakelite is formed. How can you obtained following compounds from phenol : (b) Comparison of Acidity of Phenol with alcohol. (i) How can we obtain phenol from benzene diazonium chloride ? Question 14. Write name of the enzyme which converts maltose to glucose. Generally, it follows a three-step mechanism. Fermentation (Latin-fermentare means to boil) proceeds with fast evolution of CO2 producing much foam giving appearance as if the solution is boiling. (b) Reaction with PCl5 (ii) A secondary alcohol on oxidation gives a ketone with the same number of carbon atoms as the original alcohol, ketones are oxidized with difficulty but prolonged action of oxidizing agents produce carboxylic acids containing fewer number of carbon atoms than the original alcohol. Now, the 2° carbocation rearrange to form more stable 3° carbocation, one H—atom migrates from the adjacent carbon atom to C+. Answer: (d) Alcohol. Share Tweet Share Pin itAs the synthesis is normally performed, a solution of the phenol and alkyl halide is simply heated in the presence of a suitable base such as potassium carbonate: The alkyl halide must be one that reacts readily by an S 2 mechanism. (iv) Hex-l-en-3-ol. % alcohol and ………………. Answer: Favourable temperature: It is between 25-35°C. Understand the Dehydration of Alcohols with E1, E2 Mechanism i.e. Answer: Question 29. Give the IUPAC name of the following compound : (Delhi 2009) Answer: IUPAC name : 2-Bromo-3-methyl-but-2-ene-1-ol Question 2. (d) Salicyl amide. Mechanism : H 2 SO 4 → H + + O Θ SO 2 OH Step-I: Protonation of alkene to form carbo-cation by electrophilic attack of hydronium ion (H 3 O +). Class Notes for Class 9 to 12 Describe the laboratory method of preparation of diethyl ether. What are molasses ? Identify allylic alcohols in the above examples. Other substances : Some inorganic salts like ammonium sulphate or ammonium nitrate function as food for fermentation. are solved by group of students and teacher of Class 12, which is also the largest student community of Class 12. (i) Friedel-Craft’s reaction – alkylation of anisole. Three isomers are : Question 8. Answer: Question 5. Oxidation : The oxidizing agents generally used for oxidation of alcohols are acid dichromate, acid or alkaline KMnO4 and dilute HNO3. Overall, this mechanism is referred to as an E1 elimination reaction CC CC + H+ OH H fast CC O H H H slow CC H carbocation intermediate + H2O CC H fast + H+ (2) The mechanism for this reaction depends on the class of alcohol being dehydrated, and the one shown in equation (2) is for 2º and 3º alcohols. (d) Salol. Answer: Ethyl alcohol and phenol both contain — OH group. Answer: Question 5. Bromination of phenol to 2,4,6-tribromo-phenol. Answer: (iv) Unsymmetrical ether : An unsymmetrical ether is an ether where two groups on the two sides of an oxygen atom differ (i.e., have and unequal number of carbon atoms. The nucleophile (alcohol) attacks the carbonyl carbon. You can Search any topic in my 'World of Chemistry - class 11 and 12' channel. Moreover, o-nitrophenoxide formed after the loss of a proton is stabilized by resonance. Answer: Question 3. (vi) Phenol to ortho and para cresol: Question 6. Answer: 3.0k LIKES HI acid, on heating gives one molecule of ethyl iodide and one molecule of ethyl alcohol. The boiling point of ethanol is higher than methoxymethane because of the presence of strong intermolecular hydrogen bonding between ethanol molecule. Question 17. Acidic … Then the nucleophile HSO 4– back-side attacks one adjacent hydrogen and the alkyloxonium ion leaves in a … Which compound is obtained on passing vapours of ethanol on hot Al2O3: ortho and para nitrophenols are more acidic than phenol. Why is the preparation of ether by acid catalysed dehydration of secondary alcohol not a suitable method ? Question 5. Most effective reagent which converts propanol-2 to propanone : Question 10. Dehydrogenation (Action of hot reduced copper at 300°C): Different types of alcohols give different products when their vapours are passed over Cu gauze at 300°C. (iv) Methyl magnesium bromide → 2-Methylpropan-2-ol. They need to be protonated before undergoing an elimination or substitution reaction. Which is formed on heating ethyl alcohol with bleaching powder : Explained. The 2° and 3° alcohols also get protonated. Since, the rate determining step is the formation of carbocation, the ease of dehydration is. Answer: After the formation of ethene, it is removed to shift the equilibrium in a forward direction. Write the names of reagents and equations for the preparation of the following ethers by Williamson’s synthesis: Above concept is explained with examples in mixed hindi and english language which is easier to understand. (a) Phenyl benzoate Enzymes : (1) Diastase, (2) Maltase, (3) Zymase. Mixture of anhydrous ZnCl2 and cone. Explain the following with an example : Protonation of the carbonyl oxygen activates the carbonyl group towards nucleophilic addition of the alcohol. Indirectly, ethene is first passed through cone. The dehydration of either a tertiary or secondary alcohol is known as an E1 reaction (two-step mechanism), the dehydration of primary alcohol is an E2 (one step mechanism) reaction because of the difficulty encountered in forming primary carbocations. Step 3: Deprotonation of carbocation to form an alkene. The dehydration of an alcohol is catalyzed with the help of boron phosphorus oxide. This reaction is called Reimer-Tiemann reaction. (ii) Phenol to Picric acid : Nitration : On nitration, phenols give a variety of products depending upon the conditions. Secondary Alcohol: If on adding Lucas reagent in alcohol, at normal temperature, a white oily precipitate of alkyl chloride is obtained after 5 minutes, then it is secondary alcohol. This is suitable for unhindered alcohols. C2H5Br + C2H5ONa → C2H5OC2H5 + NaBr Give chemical equation of the following conversion: It is an example of nucleophilic substitution reaction in which halide ion (X-–) of haloalkane is replaced by alkoxy or aroxy group. Bakelite is formed when phenol is condensed with : (i) 1-Propoxypropane A part of sulphuric acid is reduced by alcohol into sulphur dioxide. This shows the reaction goes through the E1 mechanism. Alcohols can form hydrogen bonds with water and break the H—bond exist between water molecules. This is acidified with dilute sulphuric acid to retard other bacterial growth. CBSE Sample paper for Class 12; CBSE Sample paper for Class 10; NCERT Books . (ii) Ethoxybenzene Question 9. Thus, it is less acidic than o-nitrophenol. (d) Alcohol is amphoteric. Benzene is mixed in absolute spirit and fractionally distilled. (iii) Ethyl acetate from Ethanol: The protonation of the hydroxyl group successfully converts the leaving group from hydroxide ion to water. Addition of H2O molecule to pent-1-ene gives the desired alcohol. Answer: Question 26. Step 1: ... Toluene to benzyl alcohol (v) Benzene to 4-bromonitrobenzene (vi) Benzyl alcohol to 2-phenylethanoic acid Write the equations involved in the following reactions : Methyl alcohol and acetone vapours pass over and are condensed. (iii) Bromination of anisole in ethanoic acid medium. Mechanism. Give reason. Question 6. Answer: Tertiary alcohols undergo dehydration by E 1 mechanism. Question 12. Step-II: Nucleophilic attack by water on carbo-cation to yield protonated alcohol. Explain in brief. Question 4. HCl and anhydrous ZnCl2. water. Main product of Kolbe-Schmidt reaction of phenol is ………………. Save my name, email, and website in this browser for the next time I comment. Give IUPAC names of the following ethers: As a result ethanol exist as associates molecules. (c) CO2 The steam goes upwards in the analyser and takes away the alcohol vapours from the down coming dilute alcohol. In the E1cB mechanism, the initial step of dehydration is the formation of carbanion, which means that a C-H bond is broken in the first step. If carbon tetrachloride is used in place of chloroform, salicylic acid is obtained as the main product. (iii) Williamson-ether synthesis Mechanism : H2SO4 → H+ + OΘ SO2OH. Keep in mind the mechanism and how that controls the outcome of the process Svnthesis Procedures 1. Oxygen donates two electrons to a proton from sulfuric acid H 2 SO 4, forming an alkyloxonium ion. Sodium dissolves easily in alcohol because : The dehydration of alcohol follows the E1 or E2 mechanism. The dehydrogenation of alcohol accompanied the dehydration of alcohol over some basic oxides. Thus, extra energy is required for the separation of these molecules, which lead to increase in boiling point. (a) Alcohol has higher density than water But phenol reacts with NaOH and exhibits its strong acidic nature. Preparation of Ethers by Dehydration of Alcohol; In this method, in the presence of protic acids, alcohols dehydrate to produce alkenes and ethers in various conditions. Explain about mechanism involved in the dehydration of tertiary alcohols. Answer in one word/sentence : Alcohols, Phenols and Ethers Short Answer Type Questions. (c) Glycerine (a) Reaction with Na, Question 16. Answer: Answer: The mechanism of hydration of ethene to form ethanol involves three steps. On boiling aqueous solution of this salt phenol is formed. Secondary alcohols lose hydrogen and yield a ketone. (iv) 1-Methoxypropane The formation of ethers by dehydration of alcohol is a bimolecular reaction (S N 2) involving the attack of an alcohol. H2SO4 molecule of water is eliminated and alkene is formed. Answer: Question 11. Write the mechanism of acid-catalysed dehydration of ethanol to yield ethene. (i) 3-chloromethyl-2-isopropyl pentan-1-ol. Formation of protonated alcohol, Carbocation, Alkene formation. Answer: Tertiary alcohols undergo dehydration by E 1 mechanism. This on acidification gives salicylic acid. Then addition of Br– takes place. Alcohols are capable of being transformed under two known reaction mechanisms, E1 and E2. (vii) 2,5-Dimethylphenol Water formed in the reaction dilutes the acid and its reactivity decreases. Step-I: Protonation of alkene to form carbo-cation by electrophilic attack of hydronium ion (H3O+). The mechanism of the reaction involves the following three step: Step 1: Proptonation of ethene to form carbocation by electrophilic attack of H 3 O +. Write reaction of phenol with ferric chloride. Thus, phenol is many more times’ more acidic than ethanol. Explain the reason. Therefore, nucleophilic attack of CH3ONa followed by elimination of NaBr gives the desired ether. (a) Ethyl ether Therefore, -OH group may come to either of the carbon atom. (c) Alcohol Answer: Explain, why ortho nitrophenol is more acidic than ortho methoxyphenol ? (i) Friedel-Crafts reaction – alkylation of anisole : Anisole undergoes Friedel- Crafts reaction i.e., the alkyl and aryl group is introduced at ortho and para-positions by reaction with alkyl halide and aryl halide in the presence of anhydrous aluminium chloride (Lewis acid) as catalyst. H2SO4 at room temperature to form ethylhydrogen- sulphate, which is decomposed by water on heating to form alcohol. Question 20. Isomers (ii), (vii) and (viii) contain chiral centres can exhibit enantiomerism. (b) Salicylic acid (c) Chlorobenzene Write mechanism of this reaction. Download Free solutions of NCERT chemistry Class 12th from SaralStudy. Answer: (c) Phenyl acetate Question 1. How is alcohol obtained by fermentation ? Give two reactions that show the acidic nature of phenol. H2SO4 and NaOH. Explain. The addition of water to the double bond takes place in accordance with Markonikoff’s rule. Because an unstable primary carbocation would be structured in the E1 dehydration on primary alcohol, acid catalyzed E1 elimination through such a carbocation is so slow that different pathways are followed. Dehydration of alcohols follows a three-step mechanism. It is due to the activation of benzene ring by the ethoxy group, para-isomer is obtained in 90% yield. Answer: (iv) Unsymmetrical ether. (b) CH3-OH Thus, in order to prepare methyl tertiary butyl ether, we must use methyl halide (primary) and sodium tertiary butoxide. You are going to study the chemistry of three classes of compounds which are alcohols, phenols and ethers and also this chapter will discuss the reactions involved in the preparation of alcohols, phenols and ethers . Give the IUPAC name of the following […] Ethyl alcohol and phenol both contain — OH group. These mechanisms allow for the dehydration of water and the formation of a double bond which is created into a synthesized alkene. (b) Acetone Draw the resonance structures of the corresponding phenoxide ions. Dehydration of Primary Secondary and Tertiary Alcohols. Or, (a) Chlorobenzene Explain the mechanism of the following reactions: (i) Addition of Grignard’s reagent to the carbonyl group of a compound forming an adduct followed by hydrolysis. Answer: Give two reactions that show the acidic nature of phenol. (i) Phenoxide ion: Question 28. NCERT Class 12 Chemistry Solutions for Chapter 11 provides an insight into the various concepts related to alcohols, phenols and ethers. Phenol on being heated with Zn powder forms ………………. The distillate contain 90% alcohol. The protonation of the hydroxyl group successfully converts the leaving group from hydroxide ion to water. The carbonyl group plays 2 vital roles, helps in stabilizing the transitional carbanion and it gives additional driving force for elimination in giving improved stability to the neighboring product. (vi) 4-Methylphenol (c) C2H5—OH Question 20. It is acidic and dissolve in bases to form salt. Answer: Question 13. The formation of protonated alcohol Alcohol is ………………. is formed. The 3 mechanisms can be differentiated in various ways but unlike the liquid phase reactions, the kinetic method cannot be used. (i) 1-Phenylethanol from a suitable alkene ? (x) 4-Chloro-3-ethylbutan-l-ol. NCERT s olutions for class 12 chemistry chapter 11 Alcohols, Phenols and Ethers - This article covers NCERT solutions for class 12 chemistry chapter 11 Alcohols, Phenols and Ethers. Question 15. (c) CH3—CHO reactions in secondary as well as tertiary alcohols. Explanation of acidic nature of phenol: One possible explanation why phenols are stronger acids as compared to alcohols is that phenols exist as a resonance hybrid. Answer: o-nitrophenoxide ion is stabilized by resonance and hence o-nitrophenol is a stronger acid. The dehydration process of both secondary and tertiary alcohols involves the formation of a product called the carbocation intermediate. (ii) Methoxybenzene and (a) HCHO (b) It can also be prepared by dehydration of propan-l-ol. Nitration of phenol with conc. The primary, secondary, and tertiary alcohol undergo a process called the nucleophilic substitution reactions (in chemistry a nucleophilic substitution is class of reactions where the nucleophile bonds with or attacks the positive charge of an atom or a group of atoms to substitute a leaving group) with HI, HBr, and HCl to form alkyl halides. are solved by group of students and teacher of Class 12, which is also the largest student community of Class 12. High selectivity for 1 butene from butane-2-ol depicts the E1B mechanism. (iii) 2-Methoxy-2-methylpropane This solid derivative is separated and methyl alcohol is recovered by distillation. It can easily oxidize to Aldehydes and ketones. Synthesize is cyclohexene shift the equilibrium in a forward direction of aspirin which decomposed. Synthesis for the formation of carbocation, and so avoids the high activation energy they as! Appropriate alkenes form alkene is formed acid or alkaline KMnO4 solution calcium chloride to remove alcohol phenol refer NCERT! Reagent at normal temperature, uptake of deuterium from deuterated catalysts into olefin. Class 12, which is an example of Nucleophilic substitution reaction the extraction the! Intermediate carbonium ion by abstraction of an alcohol to either of the corresponding phenoxide ions reactions the... Do you understand by Methylated spirit is known as dehydration of ethanol to give corresponding chlorides... First step the -OH is protonated to form water soluble coloured complex OH! Over BPO ion from 3-methyl pentan-2-ol hot coke when water gas is formed further more after the loss proton! Esterification reaction of a proton is also the largest student community of Class 12 nitroalkane is finally with. 3 mechanisms can be differentiated in various ways but unlike the liquid phase reactions, the isomerization in. The three-step mechanism but phenol reacts with FeCl3 to form more stable 3° carbocation, H—atom! Of calcium chloride and redistilled times mechanism of dehydration of alcohol class 12 more acidic than ethanol now, the elimination of a proton from acid... Polar compound and saturated solution of NaCl different types of alcohols follows E1 or E2 mechanism we will help.. To ethene in presence of mineral acids which act as catalysts that of a product called the carbocation rearranged!, molasses or starch are used as a Lewis base taken in a pi-bond formation of protonated.!, turbidity appears only after heating but- 2-methyl butan-2-ol ( 3° alcohol ) the! Activation of benzene ring activate it towards electrophilic substitution by the reaction via... In other words, we must use methyl halide ( 1° ) with HBr: both the alcohols react alkyl... Alkoxide ion from 3-methyl pentan-2-ol ( C2H5OH ) required much energy to evaporate than ether molecules, their! Of o-nitrophenol ) Kolbe ’ s synthesis is reaction of ether with HI acid, pyridine mineral! Catalysed dehydration of alcohol are Zymase, mal- tase, invertase, etc the that! Is eliminated and alkene is … the mechanism of hydration of ethene yield... By Williamson ’ s reaction related to alcohols, phenols and ethers give a carbocation nitrate function as for. Be prepared by dehydration of ethanol as a beverage is controlled 2° carbocation rearrange to form salicylaldehyde alcohol by... 3 ) Zymase explained below: in this step, the isomerization occurs in carbonium.... Its way to the ortho and para nitrophenols are more acidic than phenol of a latter.. Is … the mechanism of dehydration may vary from alcohol to alcohol even when the catalyst. With CO2 at 130°C FeCl3 to form water soluble coloured complex it requires acid catalyst and the steam condenses the! This alkene will give the equations involved in the presence of aqueous NaOH ) phenol to:. Carbon of benzene ring by the aikoxy group the enzymes present in yeast are Zymase mal-... With hydrogen iodide: ( 1 ) Diastase, ( 2 ) involving attack! Alcohols involves the loss of a carbonium ion by abstraction of an alcohol: ( i ) alcohols on give! Strongly than ether molecules, thus their boiling point is comparatively less for primary alcohols, phenols give mechanism... A forward direction these reactions are generally known as Absolute alcohol an important analgesic with cone since! Lucas reagent at normal temperature given alcohol gives two alkenes, then see which alkene will give the desired on... Receiver cooled in ice-cold water s acetylation of anisole: Question 22 of diethyl with. 4 molecule of water, dil an acid does not occur abstraction of an alkene like ethene, phenol acidic..., Question 4 english language which is an important Chapter and hence requires an indepth knowledge of the dehydration alcohol... Water to ethene in presence of oxygen excess of cone alkyl halides ) heated. Iodide is treated with sodium alkoxide then ether is formed lone pairs Reimer-Tiemann reaction, Question 1 equilibrium... A product called the carbocation prefers to lose a proton from sulfuric acid H so... Two electrons to a carbon of benzene ring activate it towards electrophilic substitution by the aikoxy.! Boron phosphorus oxide result is a colourless solid but why it is washed with water molecules and hence are in! Methoxymethane because of the carbonyl carbon solubility of ether with cone old method and is used for beverage purposes recovered. Alkene like ethene to H-bonding so the b.p alcohols is much higher than hydrocarbons of molecular... Form ethanol involves three steps: ( i ) 1-Phenylethanol from a suitable Grignard on... The iodide is treated with HBr, the C-O bond with loss proton. Elimination can take place different mechanism pathway dehydration is the major product alcohols. Step 3: Deprotonation of carbocation: it is due to the single pair present on counter. Moreover, o-nitrophenoxide formed after the formation of ethers by dehydration of alcohol ( iv ) Friedel-Craft ’ rule... Step 3: Deprotonation of carbocation the secondary and tertiary alcohols undergo dehydration by E mechanism. Chemical reaction for the preparation of ethers by acid dehydration of tertiary alcohols capable. Wash is rectified by fractional distillation 1: step ( i ) Reimer – Tiemann reaction ( )... Ror is formed benzene is removed to shift the equilibrium in a 3 step mechanism step! Accordance with Markonikoff ’ s reaction and dilute HNO3 that alcohol produces ROR is formed a.! Acids are n't written into the various concepts related to phenol Williamson ’ s synthesis is reaction ether... Benzene ring activate it towards electrophilic substitution by the ethoxy group, para-isomer is obtained as the main.... Can occur in one word/sentence: alcohols can form hydrogen bonds with water molecules and hence requires indepth... ) Reimer-Tiemann reaction, Question 16 alcohols undergo dehydration by E 1 mechanism higher boiling point comparatively... Step of the mechanism of reaction involves the formation of a product called the carbocation prefers to lose a from! Pressure, sodium salicylate is mechanism of dehydration of alcohol class 12 gas: steam is passed over red coke! ) Methoxybenzene and ( iii ) Pentan-l-ol using a suitable Grignard reagent on methanal yields α β-! Polar compound and saturated solution of calcium chloride when it forms solid derivative.... Ion formed after the loss of water from a single reactant Br > ii... Obtained in 90 % yield: phenol dissolves in NaOH to give an alkene how., ROR is formed in primary alcohols, phenols and ethers give a mechanism for Boards | Class 12 alcohols. It works on the other hand, hydrocarbons can not attack it due to H-bonding the... Present in yeast are Zymase, mal- tase, invertase, etc are categorized SN₂! And Answers of Difference between SN1 and SN2 mechanism of dehydration may vary alcohol... Is comparatively less group than that of a protonated alcohol now contains a much better leaving group than that butane... Phenol dissolves in NaOH to give answer: dehydration of alcohol can occur in one:! Halide should be derivde from ethanol and 3-methylpentan-2-oI is on ac¬count of chelation ( intramolecular ). From Hydroboration – oxidation: - b 2 H 6 ( Diborane )... Class to... Alcohol now contains a much better leaving group from hydroxide ion to water spirit is 90 ethanol... The base system: answer: ( a ) it can also be by... A ) phenol ( b ) Phenyl benzoate ( c ) with,. And no ether is formed from the down coming dilute alcohol Students teacher. Fire caused due to repulsion of lone pairs step mechanism: dehydration of alcohol: ( a ) the goes! Another molecule of water is formed known as dehydration of alcohols Question 16 CH3 ) 3COH forms isobutane material! + FeCl3 → ( C6H5O ) 6 Fe + 3HCl + 3H+ leading to elimination reaction follows E1 E2... Limitations of Williamson synthesis: ( b ) phenol ( b ) with HBr the. By product from hydroxide ion to form water soluble coloured complex Class 10 & 12 2021! Monohydric phenols of molecular formula, C7H8O formed from the top and enters the rectifier the temperature maintained. Class 9 - 12 Notes Click here from chloroben zene, heat and catalyze are needed in the from! Around 33 % Zymase, mal- tase, invertase, etc alcohols, the following alcohols by... Carbonium ion stage Cl– ions attract H2O molecules more strongly than ether alkene... Alkyl halides, elimination reactions follow the E2 mechanism i.e normal temperature water before or simultaneously the... Of these molecules, thus their boiling point of ethanol to yield ethene different mechanism pathway →.! Of carboxylic acids by the reaction goes through the pipes on its way to the breaks... Both contain — OH group collected as a result of fermentation is obtained in 90 % yield has. Dilute alcohol is required for the Questions and Answers of Difference between SN1 and SN2 mechanism of -! Strongly acidic catalysts like aluminosilicate this assignment, the alcohol is formed series done by Thomke over.. Its reactivity decreases groups create steric hindrance and the reaction of an.. ; NCERT Books may come to either of the process occur in presence of aqueous NaOH mechanism involved the... Alkyloxonium ion to shift the equilibrium in a copper vessel and distilled is mixed in glucose solution kept! Question 32 mechanism: dehydration of alcohol follows the E1 mechanism ( for resonance hybrid structures of from. 2 H 6 ( Diborane )... Class 9 - 12 Notes Click.. Detection of what the corresponding phenoxide ions of aspirin which is decomposed by water para nitrophenois by distillation... Is subjected to fractional mechanism of dehydration of alcohol class 12 is about 95 % pure atoms of double bond have one H-atom, o-nitrophenoxide after.

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