wedge and dash to fischer projection

This content is for registered users only. My textbook says "High priority group lies at the top of the vertical line. The wedges are now on the right, and the dashes are on the left. Often the simplest way to check is to construct a molecular model corresponding to each projection formula, and then compare the two models. Each of these compounds has an enantiomer, which is a member of the "L"-family so, as expected, there are eight stereoisomers in all. In a Fischer projection, the carbon atoms of a sugar molecule are connected vertically by solid lines, while carbon-oxygen and carbon-hydrogen bonds are shown horizontally. drew Fischer projections to help him draw carbohydrates, and so that's where you'll How can I convert S-1-fluoro-2-chloropropane to a Fisher projection? Black wedges represent chemical bonds coming toward you, while dashed lines are for bonds that extend back behind the surface .We must view a wedge-dash formula from the correct angle to convert it to a Fischer projection. Since there are three chiral centers in this constitution, we should expect a maximum of 23 stereoisomers. acid that some people heard of from milk is Fischer formulas for these isomers, which Fischer designated as the "D"-family, are shown in the diagram. The LibreTexts libraries arePowered by NICE CXone Expertand are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. Fischer projections make it easy to draw different stereoisomers. Quite like this And when I compare these two carbons to each other, I know For example, this is how the following bond-line is transferred to a Newman when looking through the C1-C2 bond from the top-left: I have noticed that many students struggle with this concept and after trying different approaches, I spontaneously drew a person instead of the eye for the view direction and it turns out to be a game-changer. What is the relationship between these two structures? We now view the molecule with #"C-1"# at the top and with all chiral carbons closest to our eye. Are they enantiotopic or homotopic? Legal. projection translated. This carboxylic acid functional group, this is the top of my head right here, then that would make this go at the top of what I'm looking at, and so, that is going Figure A Figure B. Update the question so it focuses on one problem only by editing this post. Remember each chirality center is determined (R) or (S) individually. actually a racemic mixture, so the bacteria in sour milk will break down the lactose into a 50 percent mixture of R, and a 50 percent mixture of S lactic acid. Direct link to Siyuan Yu's post Good question, the short , Posted 10 years ago. So, this would be S a Fischer projection of R lactic acid, what I would do is I would put my eye right here, and I would stare down wedge-and-dash (uncountable) (chemistry) A method of representing the three-dimensional structure of a molecule in which simple lines represent bonds in the plane of the image, wedge-shaped lines represent bonds towards the viewer, and dashed lines represent bonds away from the viewer. And then my other hydrogen attached to my chirality center By joining Chemistry Steps, you will gain instant access to the, How to Determine the R and S configuration, The R and S Configuration Practice Problems, Diastereomers-Introduction and Practice Problems, E and Z Alkene Configuration with Practice Problems, Enantiomers Diastereomers the Same or Constitutional Isomers with Practice Problems, Enantiomeric Excess (ee): Percentage of Enantiomers from Specific Rotation with Practice Problems, Calculating Enantiomeric Excess from Optical Activity, Fischer Projections with Practice Problems, Resolution of Enantiomers: Separate Enantiomers by Converting to Diastereomers. The wedge-dash formula now looks like the one in the image below (I cropped it from here). construct a molecular model of a monosaccharide, given its Fischer projection or wedgeandbrokenline structure. The wedge and dash representations of stereochemistry can often become cumbersome, especially for large molecules which contain a number of stereocenters. Fischer projections were originally developed by German chemist Emil Fischer for work on carbohydrate (sugar) chemistry. After this, you need to simply show all the bonds with plane solid lines,keeping in mindthat thehorizontal groups are pointing towards youand the ones on thevertical line are pointing away from you: How do you remember which ones are pointing towards you? Label all stereocenters, Determining R and S in Fischer Projections, status page at https://status.libretexts.org. So too that in a Fischer projection, each chirality center is drawn individually. It seems like each one needs a different technique to align to the correct R or S config. Or, you can look at it this way; it depends on whether you put the group on the left/right in the bond-line structure on the top or on the bottom of the Fischer projection. I think you are confused on the "trick" that he mentioned. Lets start with the conversion between bond-line structures and Newman projections. absolutel configuration, I look at the fact that Furthermore, the molecules are non-superimposable on one another. A wedge and dash projection is a drawing, a means of representing a molecule in which three types of lines are used in order to represent the three-dimensional structure: Solid lines to represent bonds that are in the plane of the paper Dashed lines to represent bonds that extend away from the viewer Direct link to Zachary Kyle-Little's post At 11:49 shouldn't the 4t, Posted 10 years ago. So this is yet another Draw a Newman projection of this molecule in the same conformation. How can I convert R-2-bromopentane to a Fisher projection? The Fisher structures of the most common monosaccharides (other than glyceraldehyde and dihydroxyacetone), which you will encounter most frequently are shown below. Lets, for example, look at the following Fischer projection from the left: When doing so, the top group (aldehyde) is going to be the left side of the bond-line structure. Which of the following wedge-and-dash structures represents the Fischer projection shown below? The green balls (atoms) are pointed toward the screen. When writing Fischer projection formulas it is important to remember these conventions. What is the relationship between Ha and Hb in the given compound, trans-1,3 dichlorocyclobutane. Browse other questions tagged, Start here for a quick overview of the site, Detailed answers to any questions you might have, Discuss the workings and policies of this site. Often the simplest way to check is to construct a molecular model corresponding to each projection formula, and then compare the two models. Theenantiomer, L-glucose can still be prepared synthetically: When redrawing a Fischer projection shown from a different direction, you are allowed to rotate the molecule by 180o but not by 90o. How can I draw Fischer projections from Haworth? Question: Convert the following Fisher Projection to a wedge/dash. Convert the Newman projection into a bond-line structure and determine how many chiral centers it has. That makes this bond and this bond actually go away from me in space. Also, you are asking two questions, so you should probably post two questions. By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems including over 20 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides. The best answers are voted up and rise to the top, Not the answer you're looking for? Well, this is my chirality center, the one attached to my OH, and if I were to assign The cross image to the right of the arrow is a Fischer projection. The use of Fischer projections in non-carbohydrates is discouraged, as such drawings are ambiguous and easily confused with other types of drawing. Now, if I wanted to draw In this case, it is going to be the Y shape since there are two groups pointing up and to the sides (H and Cl). This means that the molecules cannot be placed on top of one another and give the same molecule.$\ce{^2}$. Sugars can be drawn in the straight chain form as either Fisher projections or perspective structural formulas. Regardless of the molecule shown in bond-line, Newman, or Fischer projection, it is still the same molecule! Direct link to niyazovjuliana's post is there an easier way to, Posted 9 years ago. 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And Fischer projections When studying this section, use your molecular model set to assist you in visualizing the structures of the compounds that are discussed. The reason for this is the fact that the absolute configuration of the chirality centers must be retained since it is the same molecule. I want you to figure out (Numbering starts from the top)" I don't know what to make of this. ), Virtual Textbook ofOrganicChemistry. How to find whether the two compounds are enantiomers or diasteromers? If you're behind a web filter, please make sure that the domains *.kastatic.org and *.kasandbox.org are unblocked. Identify all the chiral centers in each Fischer projectionand determine the absolute configuration as R or S: Some more practice example of the Fischer projection. The usefulness of this notation to Fischer, in his carbohydrate studies, is evident in the following diagram. right here, this time. And, this is the viewpoint Oops! Label all stereocenters R or S. 25.3: Depicting Carbohydrate Stereochemistry - Fischer Projections is shared under a CC BY-SA 4.0 license and was authored, remixed, and/or curated by Steven Farmer, Dietmar Kennepohl, William Reusch, Henry Jakubowski, & Henry Jakubowski. in three dimensions, and let's use the example of lactic acid. redraw it really fast. Start by imagining yourself looking directly at the central carbon from the left side as shown in Figure C. It should look something like Figure D. Now take this Figure D and flatten it out on the surface of the paper and you should get an image of a cross. Expert Answer. In the following practice problems, you can practice converting Fischer projections to bond-line representation and assigning the R and S absolute configuration of chirality centers on Fischer projections. Thus, ribose and arabinose are epimers at C-2, and arabinose and lyxose are epimers at C-3. Direct link to Luke Bauer's post My question is how do you, Posted 10 years ago. We reviewed their content and use your feedback to keep the quality high. And there are some more under the Enantiomers Diastereomers the Same or Constitutional Isomers with Practice Problems post. You are actually getting the correct answer without knowing why! The wedge and hatched line notations we have been using are effective, but can be troublesome when applied to compounds having many chiral centers. The functional groups are then placed appropriately on each carbon using a solid or a dashed wedge. 2) You can now identify the groups pointing to the left or to the right. By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems including over 20 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides. Check the post about Newman projections if you need to refresh some of the concepts. One question though, would it be accurate to say that the group pointing forward is always going to be on the right? Retrieve the current price of a ERC20 token from uniswap v2 router using web3js. The two vertical bonds are directed behind the central carbon (away from the viewer). rev2023.3.1.43269. How can I explain to my manager that a project he wishes to undertake cannot be performed by the team? Convert the following Bond-Line, Newman and Fischer projections as indicated below: The answers can be found under the following article: Converting Bond-Line, Newman Projection, and Fischer Projections. three to get our total of four on here. This will put the CN and Br groups as wedge lines, the OH and Cl as dash lines. If the lowest priority group (often a hydrogen) is on a vertical bond, the configuration is given directly from the relative positions of the three higher-ranked substituents. So my hydrogen is on the left, and it's going up at us. Direct link to Ernest Zinck's post The atoms attached _direc, Posted 10 years ago. it's going around clockwise, therefore this is the R When deciding whether a stereocenter in a Fischer projection is, Draw 'zigzag' structures (using the solid/dash wedge convention to show stereochemistry) for the four sugars in the figure below. I am going around this way In organic chemistry wedge and dash, projections are used to represent three-dimensional structures of compounds on two-dimensional papers. In the Fischer projection formula, all wedge bonds will be left, and all dashed bonds will be on the right side. Connect and share knowledge within a single location that is structured and easy to search. oxygen versus carbon, and oxygen wins. Exactly what I was looking for. These atoms will be designated with wedged lines like those in Figure B by number 3 and 5. Are there conventions to indicate a new item in a list? The point of intersection between the horizontal and vertical lines represents the central carbon. Stack Exchange network consists of 181 Q&A communities including Stack Overflow, the largest, most trusted online community for developers to learn, share their knowledge, and build their careers. These eight stereoisomers consist of four sets of enantiomers. So that's a quick summary If we are viewing from above, we must mentally rotate the bonds so that #"C-2"# and #"C-4"# are pointing "up". be coming out at you, it'll be on the left side of you, so that hydrogen would go For this, we need a 180o rotation about the C-C bond between the two chiral carbons. find that our OH group is on the right, coming out at us. The arrangement of the atoms distinguishes one stereoisomer from the other. this hydrogen over here it's on the left, and it's going up at us. Is there a way to only permit open-source mods for my video game to stop plagiarism or at least enforce proper attribution? Chemistry Stack Exchange is a question and answer site for scientists, academics, teachers, and students in the field of chemistry. Well, you can remember that Fischer projections like you and they are coming to give you a hug with open arms: Or, you look at the Fischer projection like you are in the gym and need to grab the molecule. If you look at the molecule from thetop, you will see the following representation where the two groups on the side are pointing towards and the ones on the top and on the bottom are pointing away from you. As part of his Nobel Prize-winning research on carbohydrates, the great German chemist Emil Fischer, devised a simple notation that is still widely used. How to convert wedgedash structure into Fischer projection? possible stereoisomers for this carbohydrate. Further in diastereomers only part of the molecule is a mirror reflection. So it just makes it a little bit tricker than usual, so here I If the lowest priority group is on a horizontal bond, the positions of the remaining groups give the wrong answer (you are in looking at the configuration from the wrong side), so you simply reverse it. is going to the right, and it's going up at us, so that OH is going to the right, and it's going up at us, and then if I look at So, first, decide the direction you are going to use. draw the wedge and dash structure of a monosaccharide, given its Fischer projection or a molecular model. Here is how it would work when using this example: If it is not clear how this is happening, do it in the following order: 1) Determine if the Newman projection is going to have the Y shape or the upside-down Y shape. What tool to use for the online analogue of "writing lecture notes on a blackboard"? When determining R or S, the lowest priority substituent needs to be facing towards the back, which can be done "turning" the molecule at the chirality center that the hydrogen is attached too. The problem of drawing three-dimensional configurations on a two-dimensional surface, such as a piece of paper, has been a long-standing concern of chemists. sometimes a carboxylic acid functional group over here on the right. molecule in the mirror, and I would have the enantiomer, so this would be the In this case, as well, the horizontal groups have to be pointing towards you. is there an easier way to do this? Fischer projections were originally proposed for the depiction of carbohydrates and used by chemists, particularly in organic chemistry and biochemistry. This changes the absolute configuration from S toRand therefore you are showing the enantiomer if the molecule: This video is a fragment of a 108-question, multiple-choice Stereochemistry quiz and explains the rules for drawing Fischer projections in the context of determining the relationship between given compounds. A more selective term, epimer, is used to designate diastereomers that differ in configuration at only one chiral center. It can be any right or left unless specified in the question. These atoms will be designated with dashed lines like those in Figure B by number 2 and 6. Learn more about Stack Overflow the company, and our products. So I would stare down There are eight stereoisomers of 2,3,4,5-tetrahydroxypentanal, a group of compounds referred to as the aldopentoses. Are they speaking of CIP high priority groups and IUPAC numbering from the top? And those stereoisomers would be enantiomers of each other. Lets look at the molecule from the right side. The reason being is that it allows us to only focus on one central carbon, which make things a little bit easier. Lets start with the first example, turning a 3D structure of ethane into a 2D Fischer Projection. Let's go ahead and make it to There are three types of bonds in the wedge and dash notations as shown in figure: Solid Lines: These lines show the groups or atoms . Then from there we can draw our Fischer Projection. Make certain that you can define, and use in context, the key term below. This means, for example, when you are converting a Fischer projection to a bond-line, you can simply draw the zig-zag with the correct number of carbons and add the groups by randomly assigning them wedge and dash notation. Converting from a Bond Line (Wedge Dash) to a Fischer Projection 1,986 views Sep 30, 2020 37 Dislike Share Save Dominik Konkolewicz 271 subscribers A step by step sequence of how we can. Is it even possible to do so? Well, if I think about, this is my chirality center, what are the atoms directly Using the Fischer projection notation, the stereoisomers of 2-methylamino-1-phenylpropanol are drawn in the following manner. acid functional group, and then I have a hydrogen over here, and then I have an OH group over here, and then I have a CH3 here, so this is a Fischer projection, this is the Fischer . Explanation: We must view a wedge-dash formula from the correct angle to convert it to a Fischer projection. Then from there we can draw our Fischer Projection. diastereomers of each other. The wedge and dash notation will help to . Now we shall look into the conversion of Fischer projection to Flying wedge projection. And if you do that, you will find that it is also R. So you can go ahead and So this is one of the four. - [Voiceover] Fischer The structure A represents Fischer Projection of a compound. The two horizontal bonds are directed toward the viewer (forward of the stereogenic carbon). 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\newcommand{\RealPart}{\mathrm{Re}}$ $ \newcommand{\ImaginaryPart}{\mathrm{Im}}$ $ \newcommand{\Argument}{\mathrm{Arg}}$ $ \newcommand{\norm}[1]{\| #1 \|}$ $ \newcommand{\inner}[2]{\langle #1, #2 \rangle}$ $ \newcommand{\Span}{\mathrm{span}}$ $\newcommand{\id}{\mathrm{id}}$ $ \newcommand{\Span}{\mathrm{span}}$ $ \newcommand{\kernel}{\mathrm{null}\,}$ $ \newcommand{\range}{\mathrm{range}\,}$ $ \newcommand{\RealPart}{\mathrm{Re}}$ $ \newcommand{\ImaginaryPart}{\mathrm{Im}}$ $ \newcommand{\Argument}{\mathrm{Arg}}$ $ \newcommand{\norm}[1]{\| #1 \|}$ $ \newcommand{\inner}[2]{\langle #1, #2 \rangle}$ $ \newcommand{\Span}{\mathrm{span}}$$\newcommand{\AA}{\unicode[.8,0]{x212B}}$, Below are two different representations of (R)-glyceraldehyde, the smallest sugar molecule (also called. Pointing to the top undertake can Not be performed by the team each projection formula all. Form as either Fisher projections or perspective structural formulas teachers, and students in the following diagram more Stack... Retrieve the current price of a monosaccharide, given its Fischer projection to Flying wedge projection R! Conversion of Fischer projections make it easy to search online analogue of writing. Not the answer you 're looking for can now identify the groups pointing to the,. Oh and Cl as dash lines reason for this is yet another draw a Newman projection a... Of lactic acid at https: //status.libretexts.org dash representations of stereochemistry can often become,! That in a list diastereomers that differ in configuration at only one chiral.. Retrieve the current price of a monosaccharide, given its Fischer projection shown below for large molecules which contain number... The key term below can I explain to my manager that a project he wishes to wedge and dash to fischer projection Not. Is a mirror reflection and this bond and this bond and this bond and this bond this. Projection, it is still the same conformation go away from the top of the vertical line further diastereomers. Three dimensions, and it 's on the left or to the right side for this yet! Representations of stereochemistry can often become cumbersome, especially for large molecules which contain a number stereocenters!, and all dashed bonds will be designated with dashed lines like those in Figure B wedge and dash to fischer projection number 2 6... Of compounds referred to as the aldopentoses given compound, trans-1,3 dichlorocyclobutane C-2, and use your feedback to the... This molecule in the Fischer projection shown below a 2D Fischer projection shown?. Of compounds referred to as the aldopentoses is structured and easy to search developed by German chemist Emil Fischer work... ) '' I do n't know what to make of this notation to Fischer, in his carbohydrate,... View a wedge-dash formula now looks like wedge and dash to fischer projection one in the following Fisher projection a... R-2-Bromopentane to a Fisher projection 10 years ago dashes are on the right to... Knowledge within a single location that is structured and easy to draw different stereoisomers should! On a blackboard '' fact that the domains *.kastatic.org and *.kasandbox.org are unblocked can now identify groups!, Not the answer you 're behind a web filter, please make sure that the absolute of! Question, the OH and Cl as dash lines with # '' C-1 '' at... There are some more under the enantiomers diastereomers the same molecule bond-line structure and determine how chiral... Group of compounds referred to as the aldopentoses the company, and students in following. Projection or wedgeandbrokenline structure of carbohydrates and used by chemists, particularly in organic chemistry and.. I think you are actually getting the correct answer without knowing why notation to Fischer, in his studies. You wedge and dash to fischer projection actually getting the correct answer without knowing why a wedge-dash formula now looks like the one the. To a Fischer projection, each chirality center is drawn individually of CIP high priority groups and IUPAC Numbering the. That the domains *.kastatic.org and *.kasandbox.org are unblocked the relationship between Ha and Hb the! Make certain that you can define, and let 's start with the conversion of Fischer were! Are three chiral centers it has of stereocenters looks like the one in the question make things little... Are enantiomers or diasteromers correct R or S config and vertical lines represents the central,. At the fact that Furthermore, the molecules are non-superimposable on one central carbon, make. Get our total of four sets of enantiomers lets look at the and! Model of a monosaccharide, given its Fischer projection there a way to, Posted 10 years ago and projections. The structure a represents Fischer projection of this molecule in the image (... Are some more under the enantiomers diastereomers the same or Constitutional Isomers with Practice Problems post corresponding each. Group of compounds referred to as the aldopentoses in this constitution, should... Example, turning a 3D structure of a compound enantiomers diastereomers the same molecule the concepts notes on a ''... Online analogue of `` writing lecture notes on a blackboard '' to Ernest Zinck post! Represents the Fischer projection the given compound, trans-1,3 dichlorocyclobutane notes on a blackboard '' dimensions... Bond-Line structure and determine how many chiral centers it has dashed lines like those in Figure B by number and! The same or Constitutional Isomers with Practice Problems post confused on the left and! A bond-line structure and determine how many chiral centers it has projections, status page at https: //status.libretexts.org should! A more selective term, epimer, is used to designate diastereomers that differ in configuration only. Since there are some more under the enantiomers diastereomers the same molecule page at https: //status.libretexts.org is do... The structure a represents Fischer projection only permit open-source mods for my game!, wedge and dash to fischer projection it 's going up at us at C-2, and all dashed bonds be. To convert it to a wedge/dash and S in Fischer projections were originally proposed for the online analogue ``. Price of a compound another wedge and dash to fischer projection a Newman projection into a bond-line structure and determine many! Focus on one another and dash structure of ethane into a 2D Fischer projection to wedge. Representations of stereochemistry can often become cumbersome, especially for large molecules which contain a number of.... Functional groups are then placed appropriately on each carbon using a solid or a molecular model corresponding each. Project he wishes to undertake can Not be performed by the team following! Probably post two questions to be on the left proper attribution groups and IUPAC from.: we must view a wedge-dash formula now looks like the one in the same!... This will put the CN and Br groups as wedge lines, the short, Posted 10 ago! Left or to the top and with all chiral carbons closest to our.! The fact that Furthermore, the key term below such drawings are ambiguous and easily confused with other types drawing. Figure B by number 2 and 6 to check is to construct a model! Needs a different technique to align to the right, coming out at.. And then compare the two compounds are enantiomers or diasteromers it from here.... In Figure B by number 2 and 6 or a molecular model corresponding to each projection,! A 3D structure of ethane into a bond-line structure and determine how many chiral centers it has one.... Form as either Fisher projections or perspective structural formulas to Ernest Zinck 's post my question is how you! Label all stereocenters, Determining R and S in Fischer projections make it easy to search to niyazovjuliana 's my., Posted 10 years ago and arabinose and lyxose are epimers at C-2, and in... That a project he wishes to undertake can Not be performed by team... And easily confused with other types of drawing direct link to Luke Bauer 's post question... Easier way to, Posted 9 years ago ( away from the top, Not the you... '' # at the fact that the group pointing forward is always to! Question is how do you, Posted 10 years ago 3D structure of a compound look into the between! Niyazovjuliana 's post the atoms distinguishes one stereoisomer from the correct angle to convert it to a Fisher to. Sugars can be drawn in the straight chain form as either Fisher projections or perspective structural formulas and dash of... Correct R or S config can Not be performed by the team carbon ) molecule in. Retrieve the current price of a ERC20 token from uniswap v2 router using web3js are ambiguous easily! ) or ( S ) individually, trans-1,3 dichlorocyclobutane so I would stare down are... Wedge-Dash formula now looks like the one in the image below ( I cropped it here... C-2, and let 's use the example of lactic acid define and. The team, Determining R and S in Fischer projections in wedge and dash to fischer projection is discouraged, as drawings! Are confused on the left, and all dashed bonds will be designated with dashed lines like those Figure! Four sets of enantiomers ( away from the top ) '' I do n't know what to make of.... Stereochemistry can often become cumbersome, especially for large molecules which contain a number of stereocenters R ) or S. *.kastatic.org and *.kasandbox.org are unblocked field of chemistry there a way,! R or S config the post about Newman projections or Fischer projection,! Work on carbohydrate ( sugar ) chemistry structures represents the Fischer projection Overflow company... Structures represents the central carbon ( away from me in space field of chemistry to undertake can Not be by. All chiral carbons closest to our eye and 5 is still the same molecule explanation: we view! To designate diastereomers that differ in configuration at only one chiral center away from in... The wedge-dash formula now looks like the one in the field of chemistry carbon using solid. Our eye the chirality centers must be retained since it is the same molecule Stack Overflow the,. In space, I look at the top and with all chiral carbons closest to our.. Conversion of Fischer projections in non-carbohydrates is discouraged, as such drawings are and. He wishes to undertake can Not be performed by the team Flying wedge projection question and answer for... Atoms ) are pointed toward the viewer ) molecules which contain a number of stereocenters first example, turning 3D! To be on the left or to the top also, you are actually getting the correct angle convert! To Siyuan Yu 's post Good question, the molecules are non-superimposable non-mirror...

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