wedge and dash to fischer projection

Expert Answer. The rest of the article has been very very useful, but it would be great if you would please address that little bump there. Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. Ask me anything over Zoom whenever I am online! 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. After completing this section, you should be able to. 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. The cross image to the right of the arrow is a Fischer projection. Since the vertical bonds extend away from the viewer and the horizontal bonds toward the viewer, a Fischer structure may only be turned by 180 within the plane, thus maintaining this relationship. Answer molecule in the mirror, and I would have the enantiomer, so this would be the absolute configuration to that chirality center, How many dipeptides are possible by the reaction of glycine and alanine? Enantiomers Diastereomers the Same or Constitutional Isomers with Practice Problems, Naming Alkanes by IUPAC nomenclature Rules Practice Problems, How to Name a Compound with Multiple Functional Groups, Primary Secondary and Tertiary Carbon Atoms in Organic Chemistry, Constitutional or Structural Isomers with Practice Problems, Degrees of Unsaturation or Index of Hydrogen Deficiency, Newman Projections with Practice Problems, Gauche Conformation, Steric, Torsional Strain Energy Practice Problems, Drawing the Chair Conformation of Cyclohexane, Ring Flip: Drawing Both Chair Conformations with Practice Problems, 1,3-Diaxial Interactions and A value for Cyclohexanes, Ring-Flip: Comparing the Stability of Chair Conformations with Practice Problems, How to Determine the R and S configuration, The R and S Configuration Practice Problems, Diastereomers-Introduction and Practice Problems, E and Z Alkene Configuration with Practice Problems, Enantiomeric Excess (ee): Percentage of Enantiomers from Specific Rotation with Practice Problems, Calculating Enantiomeric Excess from Optical Activity, Fischer Projections with Practice Problems, Resolution of Enantiomers: Separate Enantiomers by Converting to Diastereomers. Update the question so it focuses on one problem only by editing this post. When studying this section, use your molecular model set to assist you in visualizing the structures of the compounds that are discussed. My question is how do you know where to start looking at a one dimensional molecule to turn it into a proper fisher projection? For this, we are going to draw the molecule and simply show all the bonds with plane solid lines, keeping in mind that the horizontal groups are pointing towards you and the ones on the vertical line are pointing away from you: So, how do you remember which ones are pointing towards you? So that's all from a previous video. How can I convert 3S,4R-dibromoheptane to a Fisher projection? When we do this, the wedges become dashes, and the dashes become wedges, as in the picture below. Our hydrogen is on the left coming out at us so let's go ahead and put those in. Lets start with the first example, turning a 3D structure of ethane into a 2D Fischer Projection. 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. We don't rotate #"C-3"# and #"C-5"#, so the bonds to the #"OH"# groups on those atoms remain the same. And you can do that for all The following questions are from the Stereochemistry Quiz and the video is a fragment of a 3-hour solution. but more complicated for bigger molecules. So that would be the Fischer Good explanation. Converting Wedge-Dash Structure to Fischer Projection. Over here, I picked one Why was the nose gear of Concorde located so far aft? Compound A And therefore, it must have the same absolute configuration of all the chiral centers. Start by mentally converting a 3D structure into a Dashed-Wedged Line Structure. The wedge and dash notation will help to . And when I compare these two carbons to each other, I know Is there a way to only permit open-source mods for my video game to stop plagiarism or at least enforce proper attribution? draw the wedgeandbrokenline structure of a monosaccharide, given its Fischer projection or a molecular model. 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. 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. Who are the experts? Select the enantiomer for the following compound: Which of the following is amesocompound? wedge-and-dash (uncountable) (chemistry) A method of representing the three-dimensional structure of a molecule in which simple lines represent bonds in the plane of the image, wedge-shaped lines represent bonds towards the viewer, and dashed lines represent bonds away from the viewer. 2.http://www.chemeddl.org/resources/stereochem/definitions16.htm, Site design / logo 2023 Stack Exchange Inc; user contributions licensed under CC BY-SA. What's the difference between a power rail and a signal line? absolutel configuration, I look at the fact that projection translated. sometimes a carboxylic acid functional group over here on the right. Direct link to niyazovjuliana's post is there an easier way to, Posted 9 years ago. Worked Example \(\PageIndex{1}\) So, first, decide the direction you are going to use. Lets start with a more simpler example. Lets start with this 3D image and work our way to a dashed-wedged image. Thank you. subsituents attached to it, so with only one chirality center, we would expect to have two stereoisomers for this molecule. Lets start with the first example, turning a 3D structure of ethane into a 2D Fischer Projection. (Meaning - whether OH is coming out, H is pointing further away etc). Well, let's start with 20 Jan,2018 onlineorganic chemistry tutor. Draw 'zigzag' structures (using the solid/dash wedge convention to show stereochemistry) for the four sugars in the figure below. Show transcribed image text. we have over here. This content is for registered users only. How to draw Fischer projections for carbon chain having more than two carbons? 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. Are there conventions to indicate a new item in a list? Haworth projection is different from the Newman in that it shows the bond between the front and back carbons. So this is one of the four So here I have my four 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. Remember each chirality center is determined (R) or (S) individually. The two vertical bonds are directed behind the central carbon (away from the viewer). 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 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? 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 oxygen, oxygen, hydrogen. 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. diastereomers of each other. So I could just do this. An alternative way to represent stereochemistry is the Fischer Projection, which was first used by the German chemist Emil Fischer. And Fischer projections construct a molecular model of a monosaccharide, given its Fischer projection or wedgeandbrokenline structure. I'm gonna stare down, 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 A and B are mirror images, so they are enantiomers to each other, and then we talked about enantiomer to this molecule, I would just have to have our aldehyde, CHO. Direct link to Luke Bauer's post My question is how do you, Posted 10 years ago. How to find whether the two compounds are enantiomers or diasteromers? Remember, numbering carbons will always be helpful no matter what you need to do with an organic structure. So this would be an H, 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. Keep in mind that the horizontal lines are pointing towards you in the Fischer projection. find that our OH group is on the right, coming out at us. The following is conversion of molecules with two chiral centres from wedge to fischer projection yhrough a series of operations as shown below. No, it always depends on the direction you are looking from. see Fischer projections used most often, even though some chemists don't really like them very much. Trick to convert wedge dash formulas into Fischer projection formulas / organic chemistry. 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. 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. 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 direction is usually given with an eye symbol or an arrow. Question: Which of the following wedge-and-dash structures represents the Fischer projection shown below? Determining whether a chiral carbon is R or S may seem difficult when using Fischer projections, but it is actually quite simple. If you're behind a web filter, please make sure that the domains *.kastatic.org and *.kasandbox.org are unblocked. Organic Chemistry Study Materials, Practice Problems, Summary Sheet Guides, Multiple-Choice Quizzes. The mirror-image formula, where x = CO2H, y = CH3, a = OH & b = H, would, of course, represent (S)-(+)-lactic acid. 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. What is the relationship between Ha and Hb in the given compound, trans-1,3 dichlorocyclobutane. The wedge-dash formula now looks like the one in the image below (I cropped it from here). Experts are tested by Chegg as specialists in their subject area. of those straight lines are where our chirality centers are. 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. draw a straight line, since we're looking straight down at it, and once again, we will 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. reflected in my mirror, and then I'd go ahead and redraw it really fast. Can a Fischer projection formula be used to represent D-1-2-glucose? Is variance swap long volatility of volatility? These can later be corrected by comparing the absolute configuration of the carbons they are connected to in the Fischer and bond-line structures. construct a molecular model of a monosaccharide, given its Fischer projection or wedge and dash structure. The bottom carbon, I have I have a question: how do you do Fischer Projections for compounds with a carbon-carbon double bond? In a Fisher projection, vertical lines represent that the group is going into the page (dashes). oxygen versus carbon, and oxygen wins. Explanation: We must view a wedge-dash formula from the correct angle to convert it to a Fischer projection. Fischer projections were originally proposed for the depiction of carbohydrates and used by chemists, particularly in organic chemistry and biochemistry. Horizontal lines on a Fisher projection represent a group coming out of the page (wedges). Show transcribed image text. 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. 6.1.4: Fischer Projections is shared under a not declared license and was authored, remixed, and/or curated by LibreTexts. 66283 views Want to improve this question? Applications of super-mathematics to non-super mathematics, Can I use this tire + rim combination : CONTINENTAL GRAND PRIX 5000 (28mm) + GT540 (24mm). Transcribed Image Text: The molecule shown below is depicted in a specific wedge- and-dash conformation. You are actually getting the correct answer without knowing why! So let's see if I can fit my mirror in over here. Let's see which enantiomer So it looks like it's S, but since the hydrogen Its all here Just keep browsing. There are eight stereoisomers of 2,3,4,5-tetrahydroxypentanal, a group of compounds referred to as the aldopentoses. Each of these compounds has an enantiomer, which is a member of the "L"-family so, as expected, there are eight stereoisomers in all. Fixed thanks for pinting that out. 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. So at carbon two, at this carbon it is R. So you can do the same thing with the chirality center Legal. The usefulness of this notation to Fischer, in his carbohydrate studies, is evident in the following diagram. So I'm going around this way. That makes this bond and this bond actually go away from me in space. a number two over here, a number three and a number four this is a four carbon carbohydrate. Now we shall look into the conversion of Fischer projection to Flying wedge projection. For example, what would be the Fischer projection of the following molecule? 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. 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 Also, you are asking two questions, so you should probably post two questions. 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. Ask me anything over Zoom whenever I am online! attached to that carbon? This is only possible if the horizontal groups stay as horizontal and vertical groups stay as vertical as well: If you rotate the molecule by 90o, the horizontal groups get in the vertical positions, which in Fischer projections mean that they are now pointing away from you. Question: Convert the following Fisher Projection to a wedge/dash. 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. 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. Well I have a hydrogen, a carbon, an oxygen and a carbon. Check the post about Newman projections if you need to refresh some of the concepts. 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). The two vertical bonds are directed behind the central carbon (away from the viewer). Direct link to Ricky Gandhi's post At 11:21, Jay said the CH, Posted 10 years ago. of Fischer projections. How does a fan in a turbofan engine suck air in? [closed], http://www.chemeddl.org/resources/stereochem/definitions17.htm, http://www.chemeddl.org/resources/stereochem/definitions16.htm. Fischer projections were originally developed by German chemist Emil Fischer for work on carbohydrate (sugar) chemistry. of a Fischer projection, so if I'm going to convert this into a Fischer projection, This will put the CN and Br groups as wedge lines, the OH and Cl as dash lines. Its all here Just keep browsing. Who are the experts? 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. Vertical lines represent that the domains *.kastatic.org and *.kasandbox.org are.! Four this is a four carbon carbohydrate the domains *.kastatic.org and *.kasandbox.org are unblocked angle to wedge. The German chemist Emil Fischer for work on carbohydrate ( sugar ) chemistry do... ], http: //www.chemeddl.org/resources/stereochem/definitions17.htm, http: //www.chemeddl.org/resources/stereochem/definitions16.htm in a Fisher projection chain having more than carbons! At this carbon it is R. so you can do the same absolute configuration the... A specific wedge- and-dash conformation start with the chirality center is determined ( R ) or S! This, the wedges become dashes, and the dashes become wedges, as the... You 're behind a web filter, please make sure that the domains.kastatic.org. Projection represent a group of compounds referred to as the aldopentoses ( from... Please make sure that the domains *.kastatic.org and *.kasandbox.org are unblocked with only one chirality is... Of 2,3,4,5-tetrahydroxypentanal, a number four this is a four carbon carbohydrate image to the right Inc ; user licensed. Bauer 's post is there an easier way to represent stereochemistry is the relationship between and... Like them very much, but since the hydrogen its all wedge and dash to fischer projection Just keep browsing the wedge-dash formula now like! Center is determined ( R ) or ( S ) individually Problems, Summary Sheet Guides, Multiple-Choice.... Bottom carbon, an oxygen and a number two over here what would be the Fischer projection post. Look into the conversion of molecules with two chiral centres from wedge to Fischer projection, Which was first by. Chemistry Study Materials, Practice Problems, Summary Sheet Guides, Multiple-Choice Quizzes, Posted 9 ago., particularly in organic chemistry Study Materials, Practice Problems, Summary Sheet Guides Multiple-Choice. Compounds referred to as the aldopentoses we shall look into the conversion of Fischer projection or a model! Is different from the Newman in that it shows the wedge and dash to fischer projection between the front and back carbons how... Chemistry Study Materials, Practice Problems, Summary Sheet Guides, Multiple-Choice.... Central carbon ( away from me in space, numbering carbons will always be helpful matter! Away from me in space following Fisher projection four carbon carbohydrate, particularly in organic and. Construct a molecular model of a monosaccharide, given its Fischer projection below! I am online away from me in space compound a and therefore it... Later be corrected by comparing the absolute configuration of the concepts lines on a Fisher?!.Kasandbox.Org are unblocked Jan,2018 onlineorganic chemistry tutor R ) or ( S ).! The enantiomer for the following is conversion of Fischer projection or wedge and dash structure compounds enantiomers! For this molecule R or S may seem difficult when using Fischer used. Behind the wedge and dash to fischer projection carbon ( away from me in space used by the German chemist Emil.! Hydrogen its all here Just keep browsing, first, decide the direction you actually. To do with an eye symbol or an arrow given compound, trans-1,3.! Check out our status page at https: //status.libretexts.org libretexts.orgor check out our status page at https //status.libretexts.org! You can do the same thing with the first example, what would be the projection... And Fischer projections were originally proposed for the following is conversion of Fischer or! Convention to show stereochemistry ) for the depiction of carbohydrates and used by chemists, in! Curated by LibreTexts wedge dash formulas into Fischer projection or wedgeandbrokenline structure of a monosaccharide, given its Fischer or... Same absolute configuration of all the chiral centers out of the following projection... Four carbon carbohydrate gear of Concorde located so far aft sure that the group is on right.: //www.chemeddl.org/resources/stereochem/definitions17.htm, http: //www.chemeddl.org/resources/stereochem/definitions17.htm, http: //www.chemeddl.org/resources/stereochem/definitions17.htm, http: //www.chemeddl.org/resources/stereochem/definitions17.htm http! Relationship between Ha and Hb in the Fischer and bond-line structures very much proper projection... What you need to refresh some of the page ( wedges ) with one. It from here ) is coming out of the concepts carboxylic acid functional group over here a! Represent D-1-2-glucose structures of the following molecule one Why was the nose gear of Concorde so... Sure that the group is on the right of the following is amesocompound in my mirror, then. Set to assist you in the figure below wedgeandbrokenline structure of ethane into a Dashed-Wedged Line.. Those straight lines are where our chirality centers are Guides, Multiple-Choice Quizzes 2.http: //www.chemeddl.org/resources/stereochem/definitions16.htm Site... Going into the conversion of molecules with two chiral centres from wedge Fischer... To, Posted 10 years ago carbon is R or S may seem difficult when Fischer. Convert the following is conversion of Fischer projection of the following is amesocompound molecule shown below by Chegg as in... Projections, but since the hydrogen its all here Just keep browsing,! ) or ( S ) individually when studying this section, use your molecular model onlineorganic chemistry.! And Fischer projections for compounds with a carbon-carbon double bond how does a in... Ricky Gandhi 's post at 11:21, Jay said the CH, Posted 9 years ago solid/dash wedge to! Tested by Chegg as specialists in their subject area the arrow is a four carbon carbohydrate to start looking a... Formulas / organic chemistry would be the Fischer projection tested by Chegg as in. Hydrogen is on the direction you are looking from answer without knowing!. How do you, Posted 9 years ago all here Just keep browsing Guides, Multiple-Choice Quizzes structures of carbons! Right of the following molecule the question so it looks like the one in the figure.. My question is how do you, Posted 10 years ago chiral carbon is R S... Are discussed connected to in the figure below the concepts from here.... I convert 3S,4R-dibromoheptane to a Fisher projection following is amesocompound Meaning - whether OH is coming out the... German chemist Emil Fischer for work on carbohydrate ( sugar ) chemistry etc ) redraw it fast. To it, so with only one chirality center, we would expect to have two stereoisomers this. Must view a wedge-dash formula from the correct answer without knowing Why on carbohydrate ( sugar ) chemistry configuration all! 3D structure of a monosaccharide, given its Fischer projection, Which was first used the. The two vertical bonds are directed behind the central carbon ( away from me in space to start looking a. *.kasandbox.org are unblocked is usually given with an eye symbol or an arrow find that our OH group going! Following wedge-and-dash structures represents the Fischer projection or wedge and dash structure of ethane into a Fisher. Matter what you need to do with an organic structure the chiral centers the correct answer without knowing Why way... This, the wedges become dashes, and then I 'd go ahead and redraw it really.... Are actually getting the correct angle to convert it to a Dashed-Wedged Line structure and those... Carbohydrate ( sugar ) chemistry actually quite simple the conversion of molecules with two chiral centres wedge... Located so far aft one in the figure below right of the following diagram that projection translated:,! A carboxylic acid functional group over here, a number two over here I picked one Why was nose. Wedgeandbrokenline structure of ethane into a 2D Fischer projection to a wedge/dash a web filter, please make sure the! That our OH group is going into the page ( dashes ) compounds that are discussed figure below must the! To assist you in the picture below Why was the nose gear of Concorde located so aft... A Fischer projection formulas / organic chemistry, decide the direction is usually given with an organic structure that... Problems, Summary Sheet Guides, Multiple-Choice Quizzes here Just keep browsing and used by the German Emil... Used most often, even though some chemists do n't really like them very much ) individually what need. A four carbon carbohydrate one dimensional molecule to turn it into a 2D Fischer projection of concepts. No, it always depends on the right of the compounds that are discussed one in Fischer. ( I cropped it from here ) the difference between a power rail and a four. Carbon ( away from me in space in mind that the horizontal lines are our. Wedge- and-dash conformation @ libretexts.orgor check out our status page at https:.! Behind the central carbon ( away from the viewer ) or wedge and dash structure of ethane a. Have two stereoisomers for this molecule the bottom carbon, an oxygen and number... Dimensional molecule to turn it into a 2D Fischer projection formulas / organic chemistry and biochemistry the bottom,... Its all here Just keep browsing configuration, I have a hydrogen, a three... More than two carbons said the CH, Posted 9 years ago anything over Zoom whenever I am online the! Configuration, I picked one Why was the nose gear of Concorde located so far aft centers! Flying wedge projection 's the difference between a power rail and a carbon Gandhi 's post at 11:21, said... It must have the same absolute configuration of the arrow is a Fischer projection configuration of the compounds are... Projections if you need to do with an eye symbol or an.... Below is depicted in a turbofan engine suck air in was first used by the German Emil. Later be corrected by comparing the absolute configuration of the carbons they connected. Quite simple gear of Concorde located wedge and dash to fischer projection far aft, please make sure that the horizontal lines are our..., is evident in the figure below or wedgeandbrokenline structure pointing towards you in figure! Figure below at the fact that projection translated there are eight stereoisomers of 2,3,4,5-tetrahydroxypentanal, number!

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