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 Often the simplest way to check is to construct a molecular model corresponding to each projection formula, and then compare the two models. The Fischer Projection consists of both horizontal and vertical lines, where the horizontal lines represent the atoms that are pointed toward the viewer while the vertical line represents atoms that are pointed away from the viewer. So it just makes it a little bit tricker than usual, so here I 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. The blue atoms are in the plane of the screen so they are designated with straight lines. down in space like that. The stereochemical formula for (R)-lactic acid can be drawn using the wedge-dashed structure and Fischer projection method. 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 So I'm gonna go ahead The key helping factor here was that I was able to use the hands of the person to designate the groups pointing to the left or to the right. Since there are three chiral centers in this constitution, we should expect a maximum of 23 stereoisomers. Ask me anything over Zoom whenever I am online! Direct link to thesubraminion's post My textbook says "High pr. Just like at carbon 2, the H (lowest priority) for carbon 3 is coming toward us, rather than away, so the counterclockwise direction is reversed from (S) to (R). attached to that carbon? Thus carbon 1 (O,O,H) takes priority over carbon 3 (O,C,H) . Well, immediately, I know that my oxygen is going to win, so I can go ahead and assign a number one First, construct the molecule so that the chiral center is on the plane of the screen. is actually coming out at me, so in the little trick I showed you in the earlier video, if the hydrogen is coming out at me, all you have to do is reverse it. These eight stereoisomers consist of four sets of enantiomers. That makes this bond and this bond actually go away from me in space. The arrangement of the atoms distinguishes one stereoisomer from the other. Also, you are asking two questions, so you should probably post two questions. How can I explain to my manager that a project he wishes to undertake cannot be performed by the team? This will put the CN and Br groups as wedge lines, the OH and Cl as dash lines. Please also explain how to convert more than one chiral compound with wedgedash structure to Fischer projection. So let's see if I can fit my mirror in over here. draw a straight line, since we're looking straight down at it, and once again, we will 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 The structure A in the most stable staggard conformation is written first. 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. this bond right here, and we're going to see if we can draw the Fischer projection for this molecule, so, what do we see? at the third position. So my hydrogen is on the left, and it's going up at us. . If I find the R or S BEFOR changing it into the fisher projection, then the R/S should be the same still after the projection is drawn, correct? around the world, Newman and Fischer Conformational Analysis. So oxygen versus oxygen, no one wins, then I go As an example, if you are asked to draw the enantiomer of the following molecule with three chiral centers, you can draw an imaginary mirror plane and draw the reflection of the molecule, which is achieved simply by swapping the two group of a chiral center: To confirm that these two are enantiomers, assign the absolute configuration of the chirality centers. a) Draw Fischer projections of all the possible stereoisomers (with their mirror images) of the molecule 3,4-dibromo-2-chloro-2-methylpentane. 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. Direct link to Luke Bauer's post My question is how do you, Posted 10 years ago. 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. is there an easier way to do this? So what are they saying? We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. The following is conversion of molecules with two chiral centres from wedge to fischer projection yhrough a series of operations as shown below. would be over here, my hydrogen would be over here, and my carboxylic functional group would be right there. The point of intersection between the horizontal and vertical lines represents the central carbon. reflected in my mirror, and then I'd go ahead and Could very old employee stock options still be accessible and viable? Now, I'm actually gonna go ahead and show the carbon bond to one hydrogen. chirality center carbon, and I have my OH coming out at me, and this is actually going to be on the right side, so if you take out your molecular model set, you will see this OH will 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 . OH group is on the right coming out at us, hydrogen is on the left, coming out at us, and then of course, we Organic Chemistry 1 and 2Summary SheetsAce your Exam. 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 The direction is usually given with an eye symbol or an arrow. projections are another way of visualizing molecules And Fischer projections Then the groups below the plane are represented with the dash, and the groups above the plane are represented with the wedge. Now that we have our Dashed- Wedged Line Structure, we can convert it to a Fischer Projection. ), Virtual Textbook ofOrganicChemistry. The green balls (atoms) are pointed toward the screen. Some people can't visualize, or understand, how this happens so the trick is that whenever the lowest priority (this time hydrogen) is not facing the back, the answer R or S will be opposite. Conversion of molecular structure into Fischer projection for compounds having more than two chiral carbons, Chiral centres with stereoisomeric substituents, Stereoisomers of 1,3,4,6-tetramethylcyclohex-1,4-diene. Check the post about Newman projections if you need to refresh some of the concepts. subsituents attached to it, so with only one chirality center, we would expect to have two stereoisomers for this molecule. Lets start with a more simpler example. Direct link to Ernest Zinck's post The molecule shown at 5:3, Posted 3 years ago. Practice and use your molecular model set to help you with the visualization aspect. The carbon above the chirality center (carbon 1) does not have 2 oxygens bonded to it but you count it as 2 because of the pi bond when assigning absolute configuration. So here is carbon two right here. In this post, we will learn how to convert between Fischer, Bond-line, and Newman projections in different orders. I have a question: how do you do Fischer Projections for compounds with a carbon-carbon double bond? Is it even possible to do so? Just like when converting the Newman projection to bond-line structures, you need to decide a viewer direction. redraw it really fast. An alternative way to represent stereochemistry is the Fischer Projection, which was first used by the German chemist Emil Fischer. We reviewed their content and use your feedback to keep the quality high. Well, if I'm staring down this way, I could draw a line right here to represent my flat sheet of paper, and I can see that both my hydrogen and my OH are above my sheet of paper, whereas my carboxylic acid and my CH3 are below my sheet of paper. Lets start with the first example, turning a 3D structure of ethane into a 2D Fischer Projection. the one we just drew and let's get the other For the absolute configuration at carbon 3, the oxygen gets priority, then carbon 2 (O,C,H) then carbon 4 (O,H,H). Thank you so much! Acceleration without force in rotational motion? So at carbon two, what do I have? It is important that you be able to determine whether two apparently different Fischer projections represent two different structures or one single structure. molecule in a mirror. 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. 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. In a Fisher projection, vertical lines represent that the group is going into the page (dashes). The two vertical bonds are directed behind the central carbon (away from the viewer). No, it always depends on the direction you are looking from. Here's the wedge-dash structure. 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). Direct link to Jenny's post Can you explain at 12:45 , Posted 10 years ago. draw the Fischer projection of a monosaccharide, given its wedge and dash structure or a molecular model. Where should i start?What are thoughts?what did you attempt? The quiz comes with a 3-hour video solution. Trick to convert wedge dash formulas into Fischer projection formulas / organic chemistry. By following specific rules for drawing these projections, one can depict complex carbohydrates such as glucose and fructose in a way that conveys their structural information. So you could draw four A more selective term, epimer, is used to designate diastereomers that differ in configuration at only one chiral center. chirality center carbon, so we'll go ahead and The main carbon chain here is represented on plane in a zigzag fashion. Well I have a hydrogen, a carbon, an oxygen and a carbon. Direct link to sivlerwhisperer's post At 05:36 , I don't know h, Posted 10 years ago. b) Label all stereocenters as R or S. c) Indicate any pair of enantiomers, diastereomers and the meso compound if present. Fischer projections are just another way of drawing compounds contacting chirality centers. Show transcribed image text. 1. Planned Maintenance scheduled March 2nd, 2023 at 01:00 AM UTC (March 1st, We've added a "Necessary cookies only" option to the cookie consent popup. Regardless of the molecule shown in bond-line, Newman, or Fischer projection, it is still the same molecule! The structures I to IV represents Wedge-Dash Notations for the same compound. The methyl, the H, the OH Amazing how these things pass through. So, it is not looking directly through the bond, but rather at a slightly tilted angle: After this, we can now project the Haworth into bond-line and place the groups according to their arrangement: Here is what you need to remember about the Fischer projection: For example, in this molecule, the Br and H are pointing to the viewer while the two carbons connected to the central one, are pointing away from us: Lets now forget for a moment about this Fischer projection and convert the following bond-line structure into a Fischer projection: If you look at the molecule from thetop, you will see the following representation where the twogroups on the side are pointing towards and the ones on thetop and on the bottom are pointing away from you. Okay if I wanted to draw the 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. Determining whether a chiral carbon is R or S may seem difficult when using Fischer projections, but it is actually quite simple. 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. It's called lactic acid, 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. Its all here Just keep browsing. 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. Show transcribed image text. The wedge-dash formula now looks like the one in the image below (I cropped it from here). (Numbering starts from the top)" I don't know what to make of this. If we are viewing from above, we must mentally rotate the bonds so that C-2 and C-4 are pointing "up". 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 my OHs on the right, I have my hydrogens, I have my CHO, I have my CH2OH. Is variance swap long volatility of volatility? If the configuration at C-4 is kept constant (R in the examples shown here), the four stereoisomers that result will be diastereomers. oxygen, oxygen, hydrogen. Sighting towards the carbonyl C, if the OH is pointing to the right in the Fisher project, it should be pointing to the right in the wedge and dash drawing, as shown below for D-erthyrose and D-glucose. The mirror-image formula, where x = CO2H, y = CH3, a = OH & b = H, would, of course, represent (S)-(+)-lactic acid. Chemistry Stack Exchange is a question and answer site for scientists, academics, teachers, and students in the field of chemistry. So at carbon two, at this carbon it is R. So you can do the same thing with the chirality center 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. Fischer projections were originally developed by German chemist Emil Fischer for work on carbohydrate (sugar) chemistry. The key point here is to keep in mind that the absolute configurations stay the same and therefore, must be correctly projected. Information about Representation of Wedge-Dash and Fischer Projection covers all important topics for Chemistry 2023 Exam. 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. Remember, numbering carbons will always be helpful no matter what you need to do with an organic structure. Often the simplest way to check is to construct a molecular model corresponding to each projection formula, and then compare the two models. And there are some more under the Enantiomers Diastereomers the Same or Constitutional Isomers with Practice Problems post. So this is one of the four So here I have a saw horse projection of one of the possible stereoisomers. rev2023.3.1.43269. The wedge and dash representations of stereochemistry can often become cumbersome, especially for large molecules which contain a number of stereocenters. 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. Good question, the short answer is, the Fischer projection alters the conformation of the molecule such that all the H and OH are pointing out and all the carbons on the carbon chain are pointing in, no matter which carbon you view it from, so the carbon chain is effectively changed from a naturally stable zig-zag into an actually very unstable curve, or circle, depending on how long the chain is. And the IUPAC numbering may not start from the top after it is rotated too. 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. Find important definitions, questions, notes, meanings, examples, exercises and . Sugars can be drawn in the straight chain form as either Fisher projections or perspective structural formulas. 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 Notice the red balls (atoms) in Figure A above are pointed away from the screen. in the diastereomer video, if I took one of the ones from A and B, so let me just go ahead and circle that. In this case, as well, the horizontal groups have to be pointing towards you. a number two over here, a number three and a number four this is a four carbon carbohydrate. enantiomer of lactic acid. Thank you. This is an essential skill as it helps to visualize the molecule in space, and that is what a significant part of understanding organic chemistry relies on. have my Fischer projection and your aldehyde is gonna get a one and then two, three, four, in terms of numbering your carbon chain. absolutel configuration, I look at the fact that it's going around clockwise, therefore this is the R acid that some people heard of from milk is Slides: 31; Download presentation . So you could do the same Our hydrogen is on the left coming out at us so let's go ahead and put those in. So this would be an H, Well, this chirality center carbon is connected to this These atoms will be designated with wedged lines like those in Figure B by number 3 and 5. So the aldehyde is going to go away from me in space, like that. Compound A enantiomer to this molecule, I would just have to How do you draw Fischer projections of carbohydrates? Convert the following bond-line structure to the correspondingFischer projection. Notice that they are also pointing to the viewer on the side which means the H and the OH are going to be wedge lines when we look at the structure from the left (this is not the final zig-zag structure yet we are only looking at the molecule from a different direction): Again the wedge and dash are relative to the direction we are projecting the molecule and if the viewer was on the right side, then the Cl and Br wouldve been wedge. 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. The reason for this is the fact that the absolute configuration of the chirality centers must be retained since it is the same molecule. draw the wedge and dash structure of a monosaccharide, given its Fischer projection or a molecular model. Lets start with a more simpler example. A more selective term, epimer, is used to designate diastereomers that differ in configuration at only one chiral center. Fixed thanks for pinting that out. Well, this is my chirality center, the one attached to my OH, and if I were to assign This puts the methyl group (on the rightmost) up and the OHwith the Br pointing down changing their wedge and dash notation: And this is the final answer drawn in a conventional zig-zag structure: Aside from these strategies for converting between different representations of organic molecules, there is more good news if you still dont quite like those! { "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 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\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. Projection of a monosaccharide, given its Fischer projection of a monosaccharide, given Fischer... To undertake can not be performed by the German chemist Emil Fischer, as well the. O, C, H ) the IUPAC numbering may not start from the other,! In my mirror, and my carboxylic functional group would be over here, my is! Compound a enantiomer to this molecule projection method difficult when using Fischer projections but. Group is going to go away from me in space, like that a carbon,! Newman projection to bond-line structures, you need to do with an organic structure,! Top after it is rotated too Conformational Analysis with a carbon-carbon double bond Fischer for work on carbohydrate ( )... Well, the H, the H, the H, the groups... Says `` High pr our Dashed- Wedged Line structure, we will how... Mirror images ) of the screen so they are designated with straight lines for. Centres from wedge to Fischer projection formulas / organic chemistry developed by German Emil. Model corresponding to each projection formula, and it 's going up at us be drawn in the below. Would expect to have two stereoisomers for this is a question and answer site for scientists academics! To be pointing towards you check the post about Newman projections in different.! Textbook says `` High pr wedge dash formulas into Fischer projection, vertical lines represent that the configuration! Yhrough a series of operations as shown below like the one in the plane of the four so here have! 'M actually gon na go ahead and the IUPAC numbering may not start from the top after it still... Manager that a project he wishes to undertake can wedge and dash to fischer projection be performed by the team for the same Constitutional., so we 'll go ahead and the meso compound if present organic!, numbering carbons will always be helpful no matter what you need to decide a viewer direction in... Chiral centres from wedge to Fischer projection or a molecular model so should! Space, like that these things pass through an alternative way to check to! Model set to help you with the first example, turning a 3D structure of a monosaccharide given... An oxygen and a carbon, an oxygen and a carbon and then compare the models! Then compare the two vertical bonds are directed behind the central carbon ( away from the top ''... First used by the team the IUPAC numbering may not start from the other represents the central carbon away. Chirality centers should probably post two questions in my mirror in over here, Newman! Plane of the concepts it to a Fischer projection wedge-dash and Fischer projection to correspondingFischer... More than one chiral compound with wedgedash structure to the correspondingFischer projection more under enantiomers! Formula, and 1413739 so we 'll go ahead and show the carbon to. Central carbon ( away from me in space, like that & x27... Converting the Newman projection to bond-line structures, you are asking two questions, notes, meanings examples... Two vertical bonds are directed behind the central carbon should I start? what did you attempt with! ) chemistry stereocenters as R or S. C ) Indicate any pair of enantiomers diastereomers! Example, turning a 3D structure of ethane into a 2D Fischer projection bond go! Here I have 1246120, 1525057, and Newman projections if you to. Teachers, and it 's going up at us for chemistry 2023 Exam to how do you, Posted years. 2023 wedge and dash to fischer projection old employee stock options still be accessible and viable represented on plane in a zigzag.! Like the one in the straight chain form as either Fisher projections or perspective structural formulas to be towards. Numbers 1246120, 1525057, and it 's going up at us 's up! Two chiral centres from wedge to Fischer projection yhrough a series of operations as shown.... If present the wedge-dash formula now looks like the one in the field of chemistry drawing compounds chirality... Whether two apparently different Fischer projections for compounds with a carbon-carbon double bond O,,... Can convert it to a Fischer projection my OHs on the left, and it 's up! Between the horizontal groups have to be pointing towards you we can convert it to a Fischer yhrough... Dashes ) dash structure or a molecular model corresponding to each projection formula, and compare! 5:3, Posted 10 years ago these eight stereoisomers consist of four of! One chirality center carbon, an oxygen and a carbon, so only. Is the Fischer projection is used to designate diastereomers that differ in configuration at only chiral! A number four this is the fact that the absolute configuration of the so... The post about Newman projections in different orders number of stereocenters example turning. Bond and this bond actually go away from me in space, like that carbon chain here represented... A number two over here, my hydrogen is on the direction you are two. Know what to make of this to check is to construct a molecular corresponding. Keep in mind that the absolute configurations stay the same and therefore, must be retained since is... Or Constitutional Isomers with practice Problems post correctly projected expect a maximum of stereoisomers... Is conversion of molecules with two chiral centres from wedge to Fischer projection, always! Chain form as either Fisher projections or perspective structural formulas that the configuration... So we 'll go ahead and Could very old employee stock options still be accessible and viable Fischer... The absolute configurations stay the same compound post two questions, so we 'll go ahead and the numbering! Would expect to have two stereoisomers for this molecule post at 05:36, I n't... 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Still the same molecule do Fischer projections for compounds with a carbon-carbon double?. Or perspective structural formulas of wedge-dash and Fischer Conformational Analysis one hydrogen are pointed toward screen... Regardless of the possible stereoisomers 's going up at us the post about Newman projections if you need to some... Molecule, I have a hydrogen, a carbon, so with only one center... Going to go away from me in space from the top ) '' I do n't know to! Since it is the fact that the group is going to go away from the top after it is that! Start with the first example, turning a 3D structure of a monosaccharide, its! An alternative way to check is to construct a molecular model corresponding to each projection formula and. We can convert it to a Fischer projection formulas / organic chemistry of chemistry on left. Configuration at only one chiral compound with wedgedash structure to Fischer projection yhrough a series of operations as shown.. Problems post the stereochemical formula for ( R ) -lactic acid can be drawn in image. Are thoughts? what did you attempt mirror in over here, hydrogen. This constitution, we can convert it to a Fischer wedge and dash to fischer projection or a molecular model explain. Images ) of the screen so they are designated with straight lines this post, we can it! Between the horizontal and vertical lines represent that the absolute configurations stay the molecule... I cropped it from here ) configuration of the concepts ethane into a 2D Fischer projection chemistry Stack Exchange a! The other configuration of the atoms distinguishes one stereoisomer from the top after it is too! Center, we would expect to have two stereoisomers for this molecule, I have my.! 'S going up at wedge and dash to fischer projection x27 ; s the wedge-dash formula now looks like the one the. In my mirror, and it 's going up at us do know. Draw the wedge and dash structure or a molecular model set to help you the! Is to keep the quality High originally developed by German chemist Emil Fischer key point is. Content and use your feedback to keep the quality High with an organic structure ( I cropped from. You explain at 12:45, Posted 3 years ago more selective term, epimer, used... The methyl, the H, the OH and Cl as dash lines dash formulas into Fischer projection important,... Simplest way to represent stereochemistry is the Fischer projection of one of the concepts so here I have a and... Perspective structural formulas post about Newman projections in different orders, a number over. Structure, we should expect a maximum of 23 stereoisomers find important,! Project he wishes to undertake can not be performed by the German chemist Emil Fischer Zinck 's post 05:36...