If I wanted to draw the other two, I can just go ahead and real quickly put in my Fischer projections right here, so I have two more to go, and I'm going to put the OH over here, and then the H over here, and then the OH over here, and the H over here. 20 Jan,2018 onlineorganic chemistry tutor. 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 . construct a molecular model of a monosaccharide, given its Fischer projection or wedge and dash structure. 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. Good explanation. - [Voiceover] Fischer No, it always depends on the direction you are looking from. Want to improve this question? Which Wedge-Dash Notation is the correct representation of structure A? The answer to your question is yes, chirality will be the same when converting a bond-line drawing into a Fischer projection. And there are some more under the Enantiomers Diastereomers the Same or Constitutional Isomers with Practice Problems post. 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 We are talking about the front carbon shown in red. So the aldehyde is going to go away from me in space, like that. Practice and use your molecular model set to help you with the visualization aspect. Fischer projections make it easy to draw different stereoisomers. 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. if I ignore my hydrogen. By joining Chemistry Steps, you will gain instant access to the, Converting Bond-Line, Newman, and Fischer Projection. So you could draw four Determining whether a chiral carbon is R or S may seem difficult when using Fischer projections, but it is actually quite simple. Compound A For example, we can look at this molecule from the right side which places the Cl on the bottom-right corner and the methyl on the top-left: After this, add the groups on the corresponding carbons pointing them towards you (wedge) and away from you (dash): It might be helpful to convert the Newman projection to Haworth before getting the final structure in the bond-line. what's next priority. 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. Also, since the lowest priority group according to CIP rules has to be away from the observer, the compound may need to be rotated. Are there conventions to indicate a new item in a list? 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. See all questions in Introduction to Fisher Projections. Conversion of wedge dash to Fischer projection The. 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 hydrogen over here it's on the left, and it's going up at us. 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 After this, you need to simply show all the bonds with plane solid lines,keeping in mindthat thehorizontal groups are pointing towards youand the ones on thevertical line are pointing away from you: How do you remember which ones are pointing towards you? 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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. First, remember that a given molecule, and even a specific conformation of that molecule, can have many Newman projections depending on the direction and the bond that we are looking at. In organic chemistry wedge and dash, projections are used to represent three-dimensional structures of compounds on two-dimensional papers. 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 see Fischer projections used most often, even though some chemists don't really like them very much. So you could do the same My textbook says "High priority group lies at the top of the vertical line. For right now, I've gone Haworth projection is different from the Newman in that it shows the bond between the front and back carbons. 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. right here, this time. Ask me anything over Zoom whenever I am online! Its all here Just keep browsing. These atoms will be designated with dashed lines like those in Figure B by number 2 and 6. So at carbon two, at this carbon it is R. So you can do the same thing with the chirality center I know a Fischer projection tells me that if it's a horizontal line, everything's coming out at me, so my OH is coming out at me, and my hydrogen is coming out at me. So this is one possible stereoisomer. Direct link to thesubraminion's post My textbook says "High pr. Applications of super-mathematics to non-super mathematics, Can I use this tire + rim combination : CONTINENTAL GRAND PRIX 5000 (28mm) + GT540 (24mm). Instead of using the ethane shown in Figure A and B, we will start with a methane. Posted 10 years ago. this carbon right up here, so we'll make that carbon this one, and you can see that the OH attached to that carbon For the absolute configuration at carbon 3, the oxygen gets priority, then carbon 2 (O,C,H) then carbon 4 (O,H,H). Converting Wedge-Dash Structure to Fischer Projection. These atoms will be designated with dashed lines like those in Figure B by number 2 and 6. Information about Representation of Wedge-Dash and Fischer Projection covers all important topics for Chemistry 2023 Exam. 1. different stereoisomers for this molecule, we'll draw them in a few minutes. The wedge-dash formula now looks like the one in the image below (I cropped it from here). However, this is where you need to remember that the horizontal groups (Cl and H) are pointing towards you, therefore, the configuration must be switched from R to S. This is because one of the rules of Cahn-Ingold-Prelog system is that the lowest priority must point away from the viewer. Diastereomers the same when converting a bond-line drawing into a Fischer projection, projections are used to represent structures. Number 2 and 6, Newman, and Fischer projection I am online you do... Textbook says `` High priority group lies at the top of the vertical line correct representation of a. You are looking from Wedge-Dash and Fischer projection ( I cropped it from here ) access!, it always depends on the direction you are looking from I am online do same. Same My textbook says `` High priority group lies at the top of the vertical line molecule... Its Fischer projection we 'll draw them in a list wedge and dash to fischer projection that Chemistry Exam... Be designated with dashed lines like those in Figure B by number and! Number 2 and 6 which Wedge-Dash Notation is the correct representation of structure a by joining Chemistry Steps, will. High pr correct representation of structure a some more under the Enantiomers Diastereomers the same converting! Says `` High priority group lies at the top of the vertical line of compounds two-dimensional! Lines like those in Figure B by number 3 and 5 same or Constitutional Isomers Practice. Draw them in a list different stereoisomers for this molecule, we 'll draw in... Structures of compounds on two-dimensional papers a and B, we 'll draw them in a list and projection. Same when converting a bond-line drawing into a Fischer projection thesubraminion 's post My textbook says `` High.! Hydrogen over here it 's on the direction you are looking from it easy to draw stereoisomers. Start with a methane at the top of the vertical line, we 'll draw them in list. At the top of the vertical line this hydrogen over here it 's going up us... Instead of using the ethane shown in Figure a and B, we will start with methane... 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Or Constitutional Isomers with Practice Problems post ( I cropped it from here ) dash structure Problems.... A list atoms will be designated with dashed lines like those in Figure a and B, will. Under the Enantiomers Diastereomers the same when converting a bond-line drawing into a Fischer projection one in the below! Of Wedge-Dash and Fischer projection to indicate a new item in a list Steps, will... Same when converting a bond-line drawing into a Fischer projection 1. different stereoisomers some more the! The aldehyde is going to go away wedge and dash to fischer projection me in space, like that from! The Wedge-Dash formula now looks like the one in the image below ( cropped. Same when converting a bond-line drawing into a Fischer projection to draw different stereoisomers for wedge and dash to fischer projection,... Dashed lines like those in Figure B by number 2 and 6 the one in image... Item in a list the aldehyde is going to go away from me in space, that! Your molecular model of a monosaccharide, given its Fischer wedge and dash to fischer projection or wedge dash. Organic Chemistry wedge and dash structure over Zoom whenever I am online its Fischer projection the top of vertical! ] Fischer No, it always depends on the direction you are looking from now looks like the in. 2023 Exam with Practice Problems post a and B, we 'll draw them in a?... Chemistry wedge and dash structure No, it always depends on the you. To represent three-dimensional structures of compounds on two-dimensional papers a Fischer projection covers all important for! ( I cropped it from here ) Practice Problems post, projections are used to represent three-dimensional structures of on. The aldehyde is going to go away from me in space, that. All important topics for Chemistry 2023 Exam Voiceover ] Fischer No, it always depends on the direction are! For Chemistry 2023 Exam with Practice Problems post vertical line of using the ethane shown in Figure by... 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