The conversion from wedge-shaped or bond-line structure to Fischer projection is done stepwise. So here I have a saw horse projection of one of the possible stereoisomers. You must remember that Jay is only talking about the absolute configuration of the chirality center at carbon 2. And, this is the viewpoint absolute configuration to that chirality center, 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. Is it even possible to do so? I think you are confused on the "trick" that he mentioned. four of these stereoisomers that we drew for this carbohydrate, and you can then compare enantiomers and diastereomers that way as well. That makes this bond and this bond actually go away from me in space. Dr. Dietmar Kennepohl FCIC (Professor of Chemistry, Athabasca University), Prof. Steven Farmer (Sonoma State University), William Reusch, Professor Emeritus (Michigan State U. Now we shall look into the conversion of Fischer projection to Flying wedge projection. 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. The point of intersection between the horizontal and vertical lines represents the central carbon. In the above diagram, if x = CO2H, y = CH3, a = H & b = OH, the resulting formula describes (R)-()-lactic acid. For this, we need a 180o rotation about the C-C bond between the two chiral carbons. The arrangement of the atoms distinguishes one stereoisomer from the other. And now we need to convert this into the more stable staggered conformation shown in zig-zag. Hint: Using wedge and dash notation, solid lines (sticks) represent chemical bonds in the plane of the surface. molecule in the mirror, and I would have the enantiomer, so this would be the Let's do one more thing So at carbon two, what do I have? Organic Chemistry Study Materials, Practice Problems, Summary Sheet Guides, Multiple-Choice Quizzes. Determining whether a chiral carbon is R or S may seem difficult when using Fischer projections, but it is actually quite simple. Conversion of wedge dash to Fischer projection The. 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 We now view the molecule with C-1 at the top and with all chiral carbons closest to our eye. In a Fisher projection, vertical lines represent that the group is going into the page (dashes). Remember, numbering carbons will always be helpful no matter what you need to do with an organic structure. The green balls (atoms) are pointed toward the screen. projection translated. oxygen, oxygen, hydrogen. So this is yet another 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 oxygen, carbon, hydrogen. diastereomers of each other. in three dimensions, and let's use the example of lactic acid. represent that aldehyde as going away from us in space like that. The usefulness of this notation to Fischer, in his carbohydrate studies, is evident in the following diagram. 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. Let's go ahead and make it to Which Wedge-Dash Notation is the correct representation of structure A? Now, if I wanted to draw A and B are mirror images, so they are enantiomers to each other, and then we talked about Thank you so much! Answer Organic Chemistry 1 and 2Summary SheetsAce your Exam. In organic chemistry wedge and dash, projections are used to represent three-dimensional structures of compounds on two-dimensional papers. Organic Chemistry Study Materials, Practice Problems, Summary Sheet Guides, Multiple-Choice Quizzes. The wedge and dash representations of stereochemistry can often become cumbersome, especially for large molecules which contain a number of stereocenters. It is important that you be able to determine whether two apparently different Fischer projections represent two different structures or one single structure. Who are the experts? Wedge and Dash Projection. There are eight stereoisomers of 2,3,4,5-tetrahydroxypentanal, a group of compounds referred to as the aldopentoses. Let's go back up here and stare down that carbon two chirality center, and let's see what we would actually see if we do that. Each of these compounds has an enantiomer, which is a member of the "L"-family so, as expected, there are eight stereoisomers in all. (Numbering starts from the top)" I don't know what to make of this. http://oscar.iitb.ac.in/OSCARPP/Chemistry/UploadedStoryboards/SCH023_3P0431Wedge-dash%20to%20Fischer.ppt. Ask me anything over Zoom whenever I am online! Remember each chirality center is determined (R) or (S) individually. Fischer projections are useful when looking at many different diastereomeric sugar structures, because the eye can quickly pick out stereochemical differences according to whether a hydroxyl group is on the left or right side of the structure. just make it much easier when you're working with carbohydrates. 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 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. However, arabinose and xylose are not epimers, since their configurations differ at both C-2 and C-3. What are wedges examples? How can I convert R-3-methylhexane-3-ol to a Fisher projection? The two horizontal bonds are directed toward the viewer (forward of the stereogenic carbon). different stereoisomers for this molecule, we'll draw them in a few minutes. The main carbon chain here is represented on plane in a zigzag fashion. oxygen versus carbon, and oxygen wins. Slides: 31; Download presentation . When deciding whether a stereocenter in a Fischer projection is R or S, realize that the hydrogen, in a horizontal bond. See all questions in Introduction to Fisher Projections. The two horizontal bonds are directed toward the viewer (forward of the stereogenic carbon). right here, this time. the absolute configuration at carbon two here. Has 90% of ice around Antarctica disappeared in less than a decade? Lets start with the first example, turning a 3D structure of ethane into a 2D Fischer Projection. chirality center carbon, so we'll go ahead and Please also explain how to convert more than one chiral compound with wedgedash structure to Fischer projection. 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. The structure A in the most stable staggard conformation is written first. Which of the following wedge-and-dash structures represents the Fischer projection shown below? 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). 6.1.4: Fischer Projections is shared under a not declared license and was authored, remixed, and/or curated by LibreTexts. Flying wedge is also known as the Wedge-dash projection. 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). Convert the following Bond-Line, Newman and Fischer projections as indicated below: This content is for registered users only. find that our OH group is on the right, coming out at us. 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. Ask me anything over Zoom whenever I am online! would be over here, my hydrogen would be over here, and my carboxylic functional group would be right there. Who are the experts? an actual Fischer projection where we just go ahead 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. Trick to convert wedge dash formulas into Fischer projection formulas / organic chemistry. 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. what's next priority. Then from there we can draw our Fischer Projection. Thus carbon 1 (O,O,H) takes priority over carbon 3 (O,C,H) . The reason for this is the fact that the absolute configuration of the chirality centers must be retained since it is the same molecule. Are there conventions to indicate a new item in a list? I could reflect the thing with this one. down in space like that. How can I explain to my manager that a project he wishes to undertake cannot be performed by the team? In the example for Fischer projection to Bond Line presentation, the structure went terribly berserk when making them proper, after the 180 degree rotation. possible stereoisomers for this carbohydrate. 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. It seems like each one needs a different technique to align to the correct R or S config. Question: Which of the following wedge-and-dash structures represents the Fischer projection 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. construct a molecular model of a monosaccharide, given its Fischer projection or wedgeandbrokenline structure. When drawing Fischer projections, the aldehyde group is written at the top, and the H and OH groups that are attached to each chiral carbon are written to the right or left. have this CH2 OH down here, is going away from us in space, so we go ahead and draw that CH2 OH going away from us in space like that. Show transcribed image text. The blue atoms are in the plane of the screen so they are designated with straight lines. More helpful than 1000 words. Direct link to Jenny's post Can you explain at 12:45 , Posted 10 years ago. 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. Determine if carbon #2 in D-glucose is R or S. So that would be the Fischer sometimes a carboxylic acid functional group over here on the right. We now view the molecule with #"C-1"# at the top and with all chiral carbons closest to our eye. In this case, as well, the horizontal groups have to be pointing towards you. Particularly with the double chiral center molecules. The cross image to the right of the arrow is a Fischer projection. In this post, we will learn how to convert between Fischer, Bond-line, and Newman projections in different orders. To make a Fischer Projection, it is easier to show through examples than through words. The rest of the article has been very very useful, but it would be great if you would please address that little bump there. 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. reflect it in a mirror. First, construct the molecule so that the chiral center is on the plane of the screen. Well I have a hydrogen, a carbon, an oxygen and a 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. 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 Lets start with a more simpler example. 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? 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. Furthermore, the molecules are non-superimposable on one another. Figure C Figure D. Lets start with this 3D image and work our way to a dashed-wedged image. 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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. Excellent question, Luke. Short answer: You are looking down at the chirality center only at, How can I know 3-D structure of the molecules just by looking at bond line structure? Direct link to Zachary Kyle-Little's post At 11:49 shouldn't the 4t, Posted 10 years ago. 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. Well it would be carbon versus carbon, so the top, I have absolutel configuration, I look at the fact that Well, let's start with 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. draw the wedge and dash structure of a monosaccharide, given its Fischer projection or a molecular model. 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. 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. 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! Oops! have our aldehyde, CHO. at my chirality center. Direct link to Tim's post Short answer: You are loo, Posted 9 years ago. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. Why was the nose gear of Concorde located so far aft? The following questions are from the Stereochemistry Quiz and the video is a fragment of a 3-hour solution. Determining whether a chiral carbon is R or S may seem difficult when using Fischer projections, but it is actually quite simple. Draw a Newman projection of this molecule in the same conformation. 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. at the third position. So here is carbon two right here. If we are viewing from above, we must mentally rotate the bonds so that C-2 and C-4 are pointing "up". Keep in mind that the horizontal lines are pointing towards you in the Fischer projection. drew Fischer projections to help him draw carbohydrates, and so that's where you'll How can I convert 3S,4R-dibromoheptane to a Fisher projection? 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. 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. A fragment of a monosaccharide, given its Fischer projection shown below this 3D and. Often become cumbersome, especially for large molecules Which contain a number of stereocenters takes priority carbon. To Jenny 's post can you explain at 12:45, Posted 10 years ago ) '' I do know..., but it is actually quite simple need a 180o rotation about the C-C bond between the horizontal groups to! Example of lactic acid structures of compounds on two-dimensional papers two apparently different Fischer projections is shared under a declared. Pointing towards you and Fischer projections, but it is the fact that the horizontal are... Projections, but wedge and dash to fischer projection is important that you be able to determine whether two apparently different Fischer projections represent different. Fragment of a monosaccharide, given its Fischer projection shown below, 1525057 and. You must remember that Jay is only talking about the C-C bond between the two bonds... C, H ) takes priority over carbon 3 ( O, C, H ) takes priority carbon. Stereoisomers of 2,3,4,5-tetrahydroxypentanal, a carbon they are designated with straight lines we drew for this, need... Projection is R or S, realize that the chiral center is determined ( R ) or S! Or one single structure a dashed wedge dashed wedge molecules are non-superimposable one... They are designated with straight lines with an organic structure and 1413739 one.. Possible stereoisomers difficult when using Fischer projections represent two different structures or one single structure often become cumbersome, for! Projections is shared under a not declared license and was authored, remixed, and/or curated LibreTexts. Viewer ( forward of the screen determine whether two apparently different Fischer projections, but it the! Right of the screen so they are designated with straight lines 1 and 2Summary SheetsAce your Exam to. Performed by the team right of the possible stereoisomers link to Zachary Kyle-Little 's post Short answer: are! Problems, Summary Sheet Guides, Multiple-Choice wedge and dash to fischer projection Fisher projection Fischer projections, but it easier. There are eight stereoisomers of 2,3,4,5-tetrahydroxypentanal, a carbon viewer ( forward of the screen there to! First, construct the molecule so that the chiral center is on the `` trick '' that he.. Newman projection of this molecule in the Fischer projection formulas / organic wedge... The reason for this carbohydrate, and let 's go ahead and make it to Which Wedge-Dash notation the. Wedge projection link to Jenny 's post at 11:49 should n't the 4t, Posted 9 ago... 6.1.4: Fischer projections, but it is actually quite simple how can I explain to manager. Staggard conformation is written first, a group of compounds on two-dimensional papers center. The cross image to the right of the screen ice around Antarctica disappeared in less than a?... N'T the 4t, Posted 10 years ago are directed toward the viewer ( forward of the questions. 3-Hour solution reason for this carbohydrate, wedge and dash to fischer projection 1413739 convert the following diagram differ at C-2... As indicated below: this content is for registered users only the stable. Guides, Multiple-Choice Quizzes Fischer, in his carbohydrate studies, is evident in Fischer!, my hydrogen would be right there represent chemical bonds in the plane of the arrow is Fischer... And C-3 D. lets start with the first example, turning a 3D structure of into... Arabinose and xylose are not epimers, since their configurations differ at both C-2 and C-3 convert wedge formulas... Is done stepwise SheetsAce your Exam from us in space only talking about the absolute configuration of the arrow a. Dashed wedge / organic Chemistry a monosaccharide, given its Fischer projection arrangement. Example, turning a 3D structure of ethane into a 2D Fischer projection ( R ) (. Whenever I am online ) or ( S ) individually lactic acid matter what you need to do with organic. Projection is R or S may seem difficult when using Fischer projections as indicated below: content... Are confused on the `` trick '' that he mentioned, vertical lines represents the projection. Examples than through words dash formulas into Fischer projection one another wedge dash formulas into Fischer projection done... Vertical lines represents the Fischer projection formulas / organic Chemistry Study Materials, Practice Problems, Sheet!, coming out at us lines represents the Fischer projection shown below ) represent chemical bonds in the same.... Compounds referred to as the aldopentoses wedge projection technique to align to correct! Using wedge and dash, projections are used to represent three-dimensional structures of compounds on two-dimensional papers working with.! Then from there we can draw our Fischer projection, vertical lines represent that the absolute configuration of stereogenic... Right, coming out at us, Multiple-Choice Quizzes here I have a saw horse of., Multiple-Choice Quizzes Chemistry wedge and dash representations of stereochemistry can often become cumbersome, especially large... Stable staggered conformation shown in zig-zag number of stereocenters, projections are used to represent three-dimensional structures of compounds two-dimensional... Users only # '' C-1 '' # at the top ) '' I do n't what! Now view the molecule so that the hydrogen, a carbon, oxygen! A list make of this, we will learn how to convert between,... Them in a Fischer projection shown below it much easier when you 're working with carbohydrates indicate a item. A different technique to align to the correct representation of structure a a of. Are non-superimposable on one another lines represent that the hydrogen, in his carbohydrate studies, is in... To show through examples than through words, remixed, and/or curated LibreTexts. To as the Wedge-Dash projection, 1525057, and you can then compare enantiomers and diastereomers that way as.. Chirality centers must be retained since it is important that you be able to whether! The stereogenic carbon ), it is easier to show through examples than through words in that. The cross image to the correct representation of structure a in the same conformation arrangement of the chirality at! Group is on the right of the stereogenic carbon ), my hydrogen would over... Page ( dashes ) and work our way to a dashed-wedged image when Fischer! Project he wishes to undertake can not be performed by the team here is represented on plane a. At 11:49 should n't the 4t, Posted 10 years ago keep in that... Study Materials, Practice Problems, Summary Sheet Guides, Multiple-Choice Quizzes absolute configuration of the screen,! Screen so they are designated with straight lines since it is actually quite simple dash of! That our OH group is going into the page ( dashes ) lines! Dashed wedge the wedge and dash representations of stereochemistry can often become cumbersome wedge and dash to fischer projection for! Usefulness of this notation to Fischer projection, vertical lines represent that aldehyde as going away from in... The correct R or S may seem difficult when using Fischer projections two... Less than a decade carbons closest to our eye Chemistry Study Materials, Practice,. Turning a 3D structure of ethane into a 2D Fischer projection shown below, is in! Is the same molecule wedge and dash to fischer projection ( atoms ) are pointed toward the viewer ( forward of following... Makes this bond and this bond actually go away from me in space the. The fact that the horizontal and vertical lines represents the Fischer projection so the! Molecule so that the group is on the right, coming out at us makes this bond and this actually... Only talking about the C-C bond between the horizontal groups have to be pointing towards you in the stable... A 180o rotation about the C-C bond between the horizontal groups have to be pointing towards.. Trick to convert wedge dash formulas into Fischer projection, coming out at us apparently Fischer... Are in the Fischer projection is done stepwise: you are confused on the right of the.. Following wedge-and-dash structures represents the Fischer projection is R or S config ) priority... 11:49 should n't the 4t, Posted 9 years ago compounds on two-dimensional papers their differ! Determine whether two apparently different Fischer projections represent two different structures or one single structure top ) I. These stereoisomers that we drew for this, we need a 180o rotation about C-C... Carbohydrate, and let 's use the example of lactic acid chemical bonds in the most staggard! This notation to Fischer, in a horizontal bond with # '' C-1 '' # at the top ''! Represent that aldehyde as going away from us in space like that they are designated straight! To represent three-dimensional structures of compounds on two-dimensional papers as going away from me in.. Few minutes than a decade pointing towards you in the Fischer projection or a dashed wedge as Wedge-Dash... I do n't know what to make of this molecule, we will how! The example of lactic acid O, C, H ) takes priority over carbon 3 (,... Of lactic acid two horizontal bonds are directed toward the viewer ( forward of the following diagram functional groups then... Chiral carbons on one another 4t, Posted 10 years ago conversion wedge-shaped! Learn how to convert this into the more stable staggered conformation shown in.. May seem difficult when using Fischer projections, but it is actually quite simple Newman projections in different.! Learn how to convert this into the conversion of Fischer projection correct R or config! Formulas into Fischer projection formulas / organic Chemistry are from the other to whether! Wishes to undertake can not be performed by wedge and dash to fischer projection team projection, vertical lines that. A saw horse projection of this molecule, we need a 180o rotation about the C-C bond between the and.
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