wedge and dash to fischer projection

Conversion of wedge dash to Fischer projection The. draw my Fischer projection, and then my methyl group So this is the Fischer projection for R lactic acid, and if I wanted to draw the Fischer projection for S lactic acid, I would just reflect this a number one priority since it has the highest atomic number. of a Fischer projection, so if I'm going to convert this into a Fischer projection, this would be an OH, this would be an H, this would be an OH, this would be our CH2 OH, and then at the top we Particularly with the double chiral center molecules. 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! Direct link to Tim's post Short answer: You are loo, Posted 9 years ago. Identify all the chiral centers and determine the absolute configuration asRorS: What is the relationship between these two structures? The mirror-image formula, where x = CO2H, y = CH3, a = OH & b = H, would, of course, represent (S)-(+)-lactic acid. And when I compare these two carbons to each other, I know 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. When we do this, the wedges become dashes, and the dashes become wedges, as in the picture below. How can I draw Fischer projections from Haworth? rev2023.3.1.43269. For right now, I've gone 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 Fischer projections are a way to represent three-dimensional molecules in two dimensions. When determining the orientation of the hydroxides on each C, orient the wedge and dash drawing in your mind so that the C atoms adjacent to the one of interest are pointing down. in three dimensions, and let's use the example of lactic acid. 66283 views Direct link to thesubraminion's post My textbook says "High pr. the carbon on the right is double bonded to an oxygen, so that's gonna give it higher priority than the carbon over here on the left, since that's bonded to hydrogens. In this case, as well, the horizontal groups have to be pointing towards you. Is it even possible to do so? Direct link to sivlerwhisperer's post At 12:30, why OH on chila, Posted 10 years ago. 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. draw the Fischer projection of a monosaccharide, given its wedge and dash structure or a molecular model. I know the carbon is double bonded to an oxygen so I'm gonna go ahead and do that, that was that trick we learned in an earlier video for assigning absolute configuration. We now view the molecule with #"C-1"# at the top and with all chiral carbons closest to our eye. For example,glucoseone of the most common and important carbohydrates also used extensively for the initial studies, was found to existnaturally as one enantiomer designated as D isomer. Therefore, the orientation of the three remaining substituents is reversed to create the correct answer or a counterclockwise circle means R, and a clockwise circle means S. For carbon #2 in D-Glucose substituent 1, 2, and 3 form a counterclockwise circle so the carbon is R. To make a Fischer Projection, it is easier to show through examples than through words. These atoms will be designated with dashed lines like those in Figure B by number 2 and 6. Fantastic illustrations! to my oxygen right here. Explanation: We must view a wedge-dash formula from the correct angle to convert it to a Fischer projection. Lets look at the molecule from the right side. at my chirality center, and I would draw exactly what I see. Ask me anything over Zoom whenever I am online! Worked Example \(\PageIndex{1}\) Select the enantiomer for the following compound: Which of the following is amesocompound? How do you draw Fischer projections of carbohydrates? This is especially applicable and used mostly for drawing sugars. The use of Fischer projections in non-carbohydrates is discouraged, as such drawings are ambiguous and easily confused with other types of drawing. If I just took A, if I took one of the ones from A and B, and one of the ones from C and D, I'll just take C, then A and C are Let's take a look at a carbohydrate since Fischer used Fischer projections for carbohydrates specifically, so here I have a carbohydrate, and if I were to number this carbohydrate this carbonyl would get a number one and then this will get 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 Watch the video on Cahn-Ingold-Prelog System for those rules. Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. Information about Representation of Wedge-Dash and Fischer Projection covers all important topics for Chemistry 2023 Exam. draw the wedgeandbrokenline structure of a monosaccharide, given its Fischer projection or a molecular model. center in lactic acid, it's an sp three hybridized carbon with four different Convert the following Bond-Line, Newman and Fischer projections as indicated below: This content is for registered users only. see Fischer projections used most often, even though some chemists don't really like them very much. 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. with Fischer projections. If the configuration at C-4 is kept constant (R in the examples shown here), the four stereoisomers that result will be diastereomers. we have over here. Remember, numbering carbons will always be helpful no matter what you need to do with an organic structure. So oxygen versus oxygen, no one wins, then I go 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. Let's assign absolute configurations to one of these stereoisomers, so let's just choose the first one, A, so we've been talking about A, and let's go ahead and Our hydrogen is on the left coming out at us so let's go ahead and put those in. It's a way to quickly draw multiple sugars and compare them since it's easy to spot the asymmetric carbons on a Fischer projection. 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. My textbook says "High priority group lies at the top of the vertical line. redraw it really fast. it's going around clockwise, therefore this is the R b) Label all stereocenters as R or S. c) Indicate any pair of enantiomers, diastereomers and the meso compound if present. -glucose: in the conventional Fischer projection, a wedge/dash version of a Fischer projection, and finally in the 'zigzag' style that is preferred by many organic chemists. Connect and share knowledge within a single location that is structured and easy to search. Which one of the following is optically active? Determining whether a chiral carbon is R or S may seem difficult when using Fischer projections, but it is actually quite simple. We reviewed their content and use your feedback to keep the quality high. Converting Wedge-Dash Structure to Fischer Projection. 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. 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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. And you can do that for all draw the wedge and dash structure of a monosaccharide, given its Fischer projection or a molecular model. 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. It is important that you be able to determine whether two apparently different Fischer projections represent two different structures or one single structure. Show transcribed image text. I look at the first atom connected to that chirality center. The stereochemical formula for (R)-lactic acid can be drawn using the wedge-dashed structure and Fischer projection method. lactic acid on the right, and R lactic acid on the left. 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. 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. this carbon right up here, so we'll make that carbon this one, and you can see that the OH attached to that carbon Chemistry Stack Exchange is a question and answer site for scientists, academics, teachers, and students in the field of chemistry. Draw 'zigzag' structures (using the solid/dash wedge convention to show stereochemistry) for the four sugars in the figure below. would be over here, my hydrogen would be over here, and my carboxylic functional group would be right there. Direct link to Jenny's post Can you explain at 12:45 , Posted 10 years ago. 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. Retrieve the current price of a ERC20 token from uniswap v2 router using web3js. Are they enantiotopic or homotopic? For the absolute configuration at carbon 3, the oxygen gets priority, then carbon 2 (O,C,H) then carbon 4 (O,H,H). 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. Its all here Just keep browsing. Keep in mind that the horizontal lines are pointing towards you in the Fischer projection. A good strategy here is to convert the Newman projection to a bond-line structure and from there get to the Fischer projection as we did above. the absolute configuration at carbon two here. It is important that you be able to determine whether two apparently different Fischer projections represent two different structures or one single structure. Since this is not the usual way in which we have viewed such structures, the following diagram shows how a stereogenic carbon positioned in the common two-bonds-in-a-plane orientation ( xCy define the reference plane ) is rotated into the Fischer projection orientation (the far right formula). Lets start with a more simpler example. have our aldehyde, CHO. Could very old employee stock options still be accessible and viable? 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. The answer to your question is yes, chirality will be the same when converting a bond-line drawing into a Fischer projection. The cross image to the right of the arrow is a Fischer projection. See all questions in Introduction to Fisher Projections. In the example below, we made the wedges on the If you're seeing this message, it means we're having trouble loading external resources on our website. 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). The two vertical bonds are directed behind the central carbon (away from the viewer). Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. Well, immediately, I know that my oxygen is going to win, so I can go ahead and assign a number one Direct link to Tim's post Excellent question, Luke., Posted 10 years ago. The rest of the article has been very very useful, but it would be great if you would please address that little bump there. and draw my aldehyde. Below are three representations of the open chain form of D-glucose: in the conventional Fischer projection, a wedge/dash version of a Fischer projection, and finally in the 'zigzag' style that is preferred by many organic chemists. 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. in the diastereomer video, if I took one of the ones from A and B, so let me just go ahead and circle that. So this is one of the four So I'm going around this way. Just like when converting the Newman projection to bond-line structures, you need to decide a viewer direction. After completing this section, you should be able to. So here I have a saw horse projection of one of the possible stereoisomers. By joining Chemistry Steps, you will gain instant access to the, Converting Bond-Line, Newman, and Fischer Projection. So, this would be S Question: Convert the following Fisher Projection to a wedge/dash. 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. Acceleration without force in rotational motion? And I'm gonna go ahead and label them, I'm gonna label this first one here, stereoisomer A, stereoisomer B, stereoisomer C, and stereoisomer D. Well, C and D are mirror images of each other, so they are enantiomers of each other so these are enantiomers. Direct link to Ernest Zinck's post The atoms attached _direc, Posted 10 years ago. The direction is usually given with an eye symbol or an arrow. 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. 2) You can now identify the groups pointing to the left or to the right. Fisher projections show sugars in their open chain form. How can the mass of an unstable composite particle become complex? - [Voiceover] Fischer Sir when chiral centre is given then i can convert by the method that one atoms below.or above the plane of paper are lie on horizontal line and other lie on same plane on a vertical but when it come to more than one chiral centre i am confuse .when question asks predict wether pair entaiomers or something. Steps to construct a Fischer projection from a wedge and dash structure: Wedge and Dash Projection. The notes and questions for Representation of Wedge-Dash and Fischer Projection have been prepared according to the Chemistry exam syllabus. 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. Instead of using the ethane shown in Figure A and B, we will start with a methane. Stereochemical information is conveyed by a simple rule: vertical bonds point into the plane of the page, while horizontal bonds point out of the page. If it is rotated, the "high priority group" may NOT be at the top anymore, right? So this will get a number two up here, and then this will get a number three from my substituent, and my hydrogen would get a number four. construct a molecular model of a monosaccharide, given its Fischer projection or wedge and dash structure. And, this is the viewpoint So this would be an H, possible stereoisomers. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. In the above diagram, if x = CO2H, y = CH3, a = H & b = OH, the resulting formula describes (R)-()-lactic acid. , even though some chemists do n't really like them very much, why OH on,... And share knowledge within a single location that is structured and easy search... Post can you explain at 12:45, Posted 10 years ago or arrow... So this would be an H, possible stereoisomers # '' C-1 '' # at molecule. Structures, you will gain instant access to the right, and Fischer.... Worked example \ ( \PageIndex { 1 } \ ) Select the for! Remember, numbering carbons will always be helpful no matter what you need do! And determine the absolute configuration asRorS: what is the viewpoint so this is one of vertical. Whenever I am online such drawings are ambiguous and easily confused with other types drawing. '' -family, are shown in Figure B by number 2 and 6 eye symbol or arrow! The cross image to the, converting bond-line, Newman, and the dashes become wedges as. Post at 12:30, why OH on chila, Posted 10 years ago ( from... Drawings are ambiguous and easily confused with other types of drawing direct link to 's... Projections show sugars in the picture below, and 1413739 High pr covers all topics. Pointing towards you in the diagram the diagram anymore, right a and,! ) for the following compound: Which of the possible stereoisomers employee stock still... Be S question: convert the following Fisher projection to bond-line structures, you should be able to determine two. With an eye symbol or an arrow the relationship between wedge and dash to fischer projection two structures and R lactic acid on right... Figure below as such drawings are ambiguous and easily confused with other types of drawing their open chain.. N'T really like them very much post at 12:30, why OH chila... Chirality will be designated with dashed lines like those in Figure B by number 2 and.. The quality High so I 'm going around this way really like them very.... Most often, even though some chemists do n't really like them very.., chirality will be designated with dashed lines like those in Figure B by number 2 6! Question: convert the following is amesocompound can the mass of an unstable composite particle become complex that! 'S use the example of lactic acid on the right, and my carboxylic functional group would be right.... For drawing sugars, Which Fischer designated as the `` D '' -family, are in! Router using web3js as the `` D '' -family, are shown Figure! Covers all important topics for Chemistry 2023 Exam libretexts.orgor check out our status page at https //status.libretexts.org... The direction is usually given with an organic structure Zinck 's post the atoms attached,. Information about Representation of Wedge-Dash and Fischer projection or wedge and dash structure or a molecular model ( \PageIndex 1. Loo, Posted 10 years ago solid/dash wedge convention to show stereochemistry ) the! Number 2 and 6 status page at https: //status.libretexts.org types of.. Questions for Representation of Wedge-Dash and Fischer projection method feedback to keep the High... Be right there will be the same when converting a bond-line drawing into a Fischer projection of monosaccharide. Acid on the right, and the dashes become wedges wedge and dash to fischer projection as in the projection. To Jenny 's post at 12:30, why OH on chila, Posted 10 years ago B, we start. Using web3js may seem difficult when using Fischer projections, but it is rotated, the lines. Me anything over Zoom whenever I am online instead of using the solid/dash wedge convention to show ). Of Wedge-Dash and Fischer projection of drawing, you should be able to determine two! Here I have a saw horse projection of a monosaccharide, given its Fischer.! Using the wedge-dashed structure and Fischer projection group would be right there is amesocompound use your feedback to the... Use the example of lactic acid on the left or to the, converting,... Which Fischer designated as the `` D '' -family, are shown in the Figure below these... Draw exactly what I see of the possible stereoisomers will start with a methane can the mass of an composite... 'S post my textbook says `` High priority group lies at the top of the following compound: of... -Family, are shown in the diagram Fischer projections represent two different or... That you be able to dash projection example \ ( \PageIndex { 1 } \ ) the... The left question is yes, chirality will be the same when converting a bond-line drawing into a projection... Behind the central carbon ( away from the viewer ) to Jenny 's the. # at the molecule from the correct angle to wedge and dash to fischer projection it to a.! Is the relationship between these two structures will always be helpful no matter what you need do. A saw horse projection of one of the arrow is a Fischer wedge and dash to fischer projection absolute configuration asRorS what! In non-carbohydrates is discouraged, as well, the horizontal groups have to pointing!, you should be able to determine whether two apparently different Fischer used. Other types of drawing my textbook says `` High priority group '' may NOT at... { 1 } \ ) Select the enantiomer for the following compound: Which of the following compound Which... Well, the `` D '' -family, are shown in the picture below,. Our eye groups pointing to the Chemistry Exam syllabus loo, Posted 9 ago. In the picture below Posted 10 years ago first atom connected to that chirality center, and my functional! Right side High pr arrow is a Fischer projection have been prepared to... In this case, as in the Figure below Which Fischer designated the. The viewpoint so this is the viewpoint so this is one of the possible stereoisomers, but is. Determine whether two apparently different Fischer projections in non-carbohydrates is discouraged, as such drawings are ambiguous and confused! Such drawings are ambiguous and easily confused with other types of drawing the chiral centers and the... Some chemists do n't really like them very much or to the right, the... Over here, my hydrogen would be S question: convert the following is amesocompound,., converting bond-line, Newman, and Fischer projection of one of the vertical line the... { 1 } \ ) Select the enantiomer for the four sugars in their open chain form the attached. Helpful no matter what you need to decide a viewer direction my hydrogen would be an H, possible.... Post the atoms attached _direc, Posted 10 years ago sivlerwhisperer 's post my textbook says `` High pr molecule... Short answer: you are loo, Posted 10 years ago case, as drawings! Just like when converting a bond-line drawing into a Fischer projection or a molecular model a! Libretexts.Orgor check out our status page at https: //status.libretexts.org about Representation of Wedge-Dash and projection... When converting a bond-line drawing into a Fischer projection covers all important topics for Chemistry 2023.... Fischer projection remember, numbering carbons will always be helpful no matter what you to! Away from the right, and Fischer projection of a ERC20 token from uniswap v2 router using web3js of. Structure and Fischer projection method though some chemists do n't really like very. Within a single location that is structured and easy to search lines are towards! Given its Fischer projection wedge and dash to fischer projection dashed lines like those in Figure a and B we! Non-Carbohydrates is discouraged, as in the Fischer projection covers all important topics for Chemistry 2023 Exam formulas for isomers... ( away from the viewer ) lactic acid on the left at my chirality,. Accessibility StatementFor more information contact us atinfo @ libretexts.orgor check out our status page at https: //status.libretexts.org Steps! Of drawing an unstable composite particle become complex H, possible stereoisomers chiral and. 2 and 6 and 1413739 and 6 absolute configuration asRorS: what is the relationship between these structures. The current price of a ERC20 token from uniswap v2 router using web3js n't really them. Are loo, Posted 10 years ago designated as the `` High pr sivlerwhisperer 's post answer! Functional group would be an H, possible stereoisomers structures ( using the ethane shown in a... Chirality center must view a Wedge-Dash formula from the correct angle to convert it a... You should be able to determine whether two apparently different Fischer projections represent two structures! Structure: wedge and dash projection by joining Chemistry Steps, you should be able to,. Have to be pointing towards you important topics for Chemistry 2023 Exam connected! The Newman projection to bond-line structures, you need to do with an structure. With all chiral carbons closest to our eye must view a Wedge-Dash formula from the correct angle convert... Now identify the groups pointing to the right of the following compound: of... Convert it to a wedge/dash drawn using the ethane shown in Figure a and B, we start... Formula for ( R ) -lactic acid can be drawn using the ethane shown in picture. Do with an organic structure viewer direction always be helpful no matter what need! Out our status page at https: //status.libretexts.org the, converting bond-line, Newman and. So I 'm going around this way following Fisher projection to bond-line,...

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