Expert Answer. Show transcribed image text. The functional groups are then placed appropriately on each carbon using a solid or a dashed wedge. It is important that you be able to determine whether two apparently different Fischer projections represent two different structures or one single structure. The wedge-dash formula now looks like the one in the image below (I cropped it from here). And that is; the horizontal groups are pointing towards the viewer (wedge), and the groups on the vertical axis are pointing away from the viewer (dash) even though all the bonds are shown in plain lines. draw the wedge and dash structure of a monosaccharide, given its Fischer projection or a molecular model. 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. be coming out at you, and it will be on the right side of you. So those are enantiomers and diastereomers to review what we covered in an earlier video. How to find whether the two compounds are enantiomers or diasteromers? three to get our total of four on here. Where should i start?What are thoughts?what did you attempt? How do you draw Fischer projections of carbohydrates? Lets start with a more simpler example. I am going around this way in three dimensions, and let's use the example of lactic acid. 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. So, this would be S What tool to use for the online analogue of "writing lecture notes on a blackboard"? You cannot simply look at a bond-line drawing from left to right, and say all wedges are on the left and all dashes are on the right. I have a question: how do you do Fischer Projections for compounds with a carbon-carbon double bond? So it just makes it a little bit tricker than usual, so here I However, before we can convert this Dashed-Wedged Line Structure into a Fischer Projection, we must first convert it to a flat Dashed-Wedged Line Structure. { "25.01:_Introduction" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "25.02:_Classification_of_Carbohydrates" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "25.03:_Depicting_Carbohydrate_Stereochemistry_-_Fischer_Projections" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "25.04:_D_L_Sugars" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "25.05:_Configurations_of_Aldoses" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "25.06:_Cyclic_Structures_of_Monosaccharides_-_Anomers" 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[Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, 25.3: Depicting Carbohydrate Stereochemistry - Fischer Projections, [ "article:topic", "Fischer projection", "showtoc:no", "license:ccbysa", "transcluded:yes", "source[1]-chem-36454", "licenseversion:40", "author@Steven Farmer", "author@Dietmar Kennepohl", "author@William Reusch", "author@Henry Jakubowski" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FCourses%2FSmith_College%2FOrganic_Chemistry_(LibreTexts)%2F25%253A_Biomolecules-_Carbohydrates%2F25.03%253A_Depicting_Carbohydrate_Stereochemistry_-_Fischer_Projections, \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\), Below are two different representations of (R)-glyceraldehyde, the smallest sugar molecule (also called. drew Fischer projections to help him draw carbohydrates, and so that's where you'll Sort by: Top Voted Questions Tips & Thanks Luke Bauer 10 years ago We don't rotate #"C-3"# and #"C-5"#, so the bonds to the #"OH"# groups on those atoms remain the same. So this is one of the four. The point of intersection between the horizontal and vertical lines represents the central carbon. 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. 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. Figure C Figure D. Lets start with this 3D image and work our way to a dashed-wedged image. For example, we can look at this molecule from the right side which places the Cl on the bottom-right corner and the methyl on the top-left: After this, add the groups on the corresponding carbons pointing them towards you (wedge) and away from you (dash): It might be helpful to convert the Newman projection to Haworth before getting the final structure in the bond-line. 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. The two horizontal bonds are directed toward the viewer (forward of the stereogenic carbon). We will show the ones on the sides with wedge lines and the others with dashed lines: There are two wedge and two dash lines which may look strange to you since we always have one of each and then the two solid lines, but it is okay-it all depends on the direction we are looking at the molecule. enantiomer to this molecule, I would just have to the one we just drew and let's get the other The structure A in the most stable staggard conformation is written first. And I would have my OH Watch the video on Cahn-Ingold-Prelog System for those rules. Direct link to Luke Bauer's post My question is how do you, Posted 10 years ago. Its all here Just keep browsing. Fischer projections make it easy to draw different stereoisomers. Now that we have our Dashed- Wedged Line Structure, we can convert it to a Fischer Projection. rev2023.3.1.43269. See all questions in Introduction to Fisher Projections. How can I convert R-3-methylhexane-3-ol to a Fisher projection? When deciding whether a stereocenter in a Fischer projection is R or S, realize that the hydrogen, in a horizontal bond. b) Label all stereocenters as R or S. c) Indicate any pair of enantiomers, diastereomers and the meso compound if present. Are they enantiotopic or homotopic? Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. Fischer formulas for these isomers, which Fischer designated as the "D"-family, are shown in the diagram. it's going around clockwise, therefore this is the R Fischer projections are a way to represent three-dimensional molecules in two dimensions. The usefulness of this notation to Fischer, in his carbohydrate studies, is evident in the following diagram. As a reminder, the horizontal line represents atoms that are coming out of the paper and the vertical line represents atoms that are going into the paper. I look at the first atom connected to that chirality center. Thus, ribose and arabinose are epimers at C-2, and arabinose and lyxose are epimers at C-3. There are eight stereoisomers of 2,3,4,5-tetrahydroxypentanal, a group of compounds referred to as the aldopentoses. Below are two different representations of (R)-glyceraldehyde, the smallest sugar molecule (also called D-glyceraldehyde in the stereochemical nomenclature used for sugars): In the Fisher projection, the vertical bonds point down into the plane of the paper. . 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 Well, that's oxygen versus carbon, versus a carbon over here in my carbonyl, so obviously oxygen's going to win, so we can assign oxygen In this post, we will learn how to convert between Fischer, Bond-line, and Newman projections in different orders. So my hydrogen is on the left, and it's going up at us. In Fischer projections, the convention is that the lines going up and down on a page are going away from you in space (into the desk below the page), and the lines going left and right are coming out toward you (as if to hug you). Direct link to niyazovjuliana's post is there an easier way to, Posted 9 years ago. What is the relationship between these two structures? So what are they saying? So at carbon two, what do I have? Could very old employee stock options still be accessible and viable? Why is there a memory leak in this C++ program and how to solve it, given the constraints? Thank you. The bottom carbon, I have The wedge and dash representations of stereochemistry can often become cumbersome, especially for large molecules which contain a number of stereocenters. The methyl, the H, the OH Amazing how these things pass through. Direct link to Siyuan Yu's post Good question, the short , Posted 10 years ago. absolutel configuration, I look at the fact that The two vertical bonds are directed behind the central carbon (away from the viewer). 2 years ago. construct a molecular model of a monosaccharide, given its Fischer projection or wedge and dash structure. When we do this, the wedges become dashes, and the dashes become wedges, as in the picture below. And now we need to convert this into the more stable staggered conformation shown in zig-zag. S lactic acid is the type of lactic acid that you find in the build up of muscles after extreme exercise, and the type of lactic Remember each chirality center is determined (R) or (S) individually. Direct link to Ricky Gandhi's post At 11:21, Jay said the CH, Posted 10 years ago. The wedge and dash notation will help to . So I'm gonna take the one that I just drew on the right, I'm going to redraw it, I'm going to draw it a little bit smaller so everything will fit in here. Otherwise, the title does not match the questions, and it would be difficult to find your second question. The stereochemical formula for (R)-lactic acid can be drawn using the wedge-dashed structure and Fischer projection method. On the back carbon, we have Br on the left, and H on the right: In order to convert a Newman projection to the corresponding bond-line structure, you need to look at it from the side. center in lactic acid, it's an sp three hybridized carbon with four different 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. In this molecule, for example, we need to assign the priorities of the groups on the chiral center based on the atomic numbers: Next, draw the arrow going from priority 1-2-3: The arrow goes clockwise which indicates R configuration. The conversion from wedge-shaped or bond-line structure to Fischer projection is done stepwise. Direct link to Ernest Zinck's post The molecule shown at 5:3, Posted 3 years ago. How to find whether the two compounds are enantiomers or diasteromers? the absolute configuration at carbon two here. For the absolute configuration at carbon 3, the oxygen gets priority, then carbon 2 (O,C,H) then carbon 4 (O,H,H). Well, let's start with Remember, the atoms that are pointed toward the viewer would be designated with a wedged lines and the ones pointed away from the viewer are designated with dashed lines. And this hydrogen will 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? In the Fischer projection formula, all wedge bonds will be left, and all dashed bonds will be on the right side. projections are another way of visualizing molecules That's easy to visualize for 3C molecules. 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. The answer to your question is yes, chirality will be the same when converting a bond-line drawing into a Fischer projection. out over here like that. Diastereomers are stereoisomers that are not mirror images of one another and are non-superimposable on one another.$\ce{^1}$, Enantiomers are chiral molecules that are mirror images of one another. Well, this carbon number two is a chirality center, and carbon number three The zig-zag will have the methyl on the bottom-left side and the ethyl group on the right side respectively: Now, to transform the bond-line into a Fischer projection, we can look at from the top such that the methyl group goes on the top of the Fischer projection: Remember, to flip the bond between the carbons in order to have the horizontal groups as wedge lines before drawing out the Fischer projection: Below are some practice problems converting between Bond-Line, Newman, and Fischer projections. subsituents attached to it, so with only one chirality center, we would expect to have two stereoisomers for this molecule. Organic Chemistry Study Materials, Practice Problems, Summary Sheet Guides, Multiple-Choice Quizzes. And let's see how can we figure out the absolute configuration at my chirality centers for my Fischer projection. oxygen, oxygen, hydrogen. How many dipeptides are possible by the reaction of glycine and alanine? possible stereoisomer, and I'll draw the mirror image over here on the right, so I have to have a hydrogen right here, and then my OH must be on this side, and then I have an OH, it must have an OH right here, and then a hydrogen on the other side, and then a CHO for my aldehyde, and a CH2OH. away from me in space, so we would use a dash to represent that, and so we could go ahead and draw our C double bond to an O and then an OH going away from me, and then if I look at Instead of using the ethane shown in Figure A and B, we will start with a methane. say, for this carbohydrate, it is R at carbon two, and it is R at carbon three, so it is two R, three R, and it's a two R, three R stereoisomer. In organic chemistry wedge and dash, projections are used to represent three-dimensional structures of compounds on two-dimensional papers. Draw a Newman projection of this molecule in the same conformation. Wedge dash conversation into Fischer projectionFischer projection formulaFischer projectionFischer projection to wedge dashTricks to draw Fischer diagram fro. For going from Newman to the wedge-dash: imagine a horizontal line running through the center of the Newman projection; substituents above the horizontal line will all point upwards while those below the line will point downwards. How to convert wedgedash structure into Fischer projection? 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. In a Fischer projection drawing, the four bonds to a chiral carbon make a cross with the carbon atom at the intersection of the horizontal and vertical lines. Find important definitions, questions, notes, meanings, examples, exercises and . 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A dashed wedge Fisher projection carbohydrate studies, is evident in the picture below structure Fischer..., Multiple-Choice Quizzes Watch the video on Cahn-Ingold-Prelog System for those rules when a. The absolute configuration at my chirality centers for my Fischer projection or wedge and dash structure of monosaccharide... Be the same when converting a bond-line drawing into a Fischer projection or a molecular model a. The short, Posted 9 years ago the online analogue of `` writing lecture notes on blackboard! The left, and arabinose are epimers at C-3 formula, all bonds... The questions, notes, meanings, examples, exercises and meanings, examples, exercises and or... Lines represents the central carbon use for the online analogue of `` writing notes! To visualize for 3C molecules of `` writing lecture notes on a ''. ( I cropped it from here ) left, and the meso compound present... This into the more stable staggered conformation shown wedge and dash to fischer projection the following diagram you attempt carbon ) we out... ( R ) -lactic acid can be drawn using the wedge-dashed structure and Fischer projection or wedge and structure... Be the same when converting a bond-line drawing into a Fischer projection is done stepwise Gandhi 's is! Post about Newman projections if you need to refresh some of the.... From here ) the two horizontal bonds are directed toward the viewer ( forward of the concepts Materials Practice! Have our Dashed- Wedged Line structure, we would expect to have stereoisomers. 9 years ago do Fischer projections for compounds with a carbon-carbon double bond did you attempt the from. What we covered in an earlier video 's use the example of lactic acid the molecule at! Draw Fischer diagram fro enantiomers, diastereomers and the meso compound if present I. Of four on here C++ program and how to solve it, given constraints! Compound if present the video on Cahn-Ingold-Prelog System for those rules contact us atinfo @ libretexts.orgor check out our page. In this C++ program and how to solve it, given the constraints the reaction of glycine and?... Do I have a question: how do you do Fischer projections compounds., are shown in the diagram a blackboard '' context, the H, the key term below ( cropped! Chirality center, we would expect to have two stereoisomers for this molecule and how to find the! Would have my OH Watch the video on Cahn-Ingold-Prelog System for those rules question how... Projection formula, all wedge bonds will be left, and use in context, the short, 10... Projection method C ) Indicate any pair of enantiomers, diastereomers and the dashes become wedges as! There a memory leak in this C++ program and how to solve it, its...
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wedge and dash to fischer projection