Now that we understand the differences in energy between the different rotations of a Newman Projection, I want to really go in-depth on how to draw and interpret a Newman Projection. Alright? So there is a method to the madness and it's just a series of steps that I want to teach you. Alright? So let's say that you have the following example. This is a very common problem that you could see on your exam. Draw the most energetically favorable Newman Projection for that 5 carbon chain down the C2, C3 bond. Okay? So how do we even begin to approach this? We need to use steps.
- 1. A Review of General Chemistry5h 5m
- Summary23m
- Intro to Organic Chemistry5m
- Atomic Structure16m
- Wave Function9m
- Molecular Orbitals17m
- Sigma and Pi Bonds9m
- Octet Rule12m
- Bonding Preferences12m
- Formal Charges6m
- Skeletal Structure14m
- Lewis Structure20m
- Condensed Structural Formula15m
- Degrees of Unsaturation15m
- Constitutional Isomers14m
- Resonance Structures46m
- Hybridization23m
- Molecular Geometry16m
- Electronegativity22m
- 2. Molecular Representations1h 14m
- 3. Acids and Bases2h 46m
- 4. Alkanes and Cycloalkanes4h 19m
- IUPAC Naming29m
- Alkyl Groups13m
- Naming Cycloalkanes10m
- Naming Bicyclic Compounds10m
- Naming Alkyl Halides7m
- Naming Alkenes3m
- Naming Alcohols8m
- Naming Amines15m
- Cis vs Trans21m
- Conformational Isomers13m
- Newman Projections14m
- Drawing Newman Projections16m
- Barrier To Rotation7m
- Ring Strain8m
- Axial vs Equatorial7m
- Cis vs Trans Conformations4m
- Equatorial Preference14m
- Chair Flip9m
- Calculating Energy Difference Between Chair Conformations17m
- A-Values17m
- Decalin7m
- 5. Chirality3h 39m
- Constitutional Isomers vs. Stereoisomers9m
- Chirality12m
- Test 1:Plane of Symmetry7m
- Test 2:Stereocenter Test17m
- R and S Configuration43m
- Enantiomers vs. Diastereomers13m
- Atropisomers9m
- Meso Compound12m
- Test 3:Disubstituted Cycloalkanes13m
- What is the Relationship Between Isomers?16m
- Fischer Projection10m
- R and S of Fischer Projections7m
- Optical Activity5m
- Enantiomeric Excess20m
- Calculations with Enantiomeric Percentages11m
- Non-Carbon Chiral Centers8m
- 6. Thermodynamics and Kinetics1h 22m
- 7. Substitution Reactions1h 48m
- 8. Elimination Reactions2h 30m
- 9. Alkenes and Alkynes2h 9m
- 10. Addition Reactions3h 18m
- Addition Reaction6m
- Markovnikov5m
- Hydrohalogenation6m
- Acid-Catalyzed Hydration17m
- Oxymercuration15m
- Hydroboration26m
- Hydrogenation6m
- Halogenation6m
- Halohydrin12m
- Carbene12m
- Epoxidation8m
- Epoxide Reactions9m
- Dihydroxylation8m
- Ozonolysis7m
- Ozonolysis Full Mechanism24m
- Oxidative Cleavage3m
- Alkyne Oxidative Cleavage6m
- Alkyne Hydrohalogenation3m
- Alkyne Halogenation2m
- Alkyne Hydration6m
- Alkyne Hydroboration2m
- 11. Radical Reactions1h 58m
- 12. Alcohols, Ethers, Epoxides and Thiols2h 42m
- Alcohol Nomenclature4m
- Naming Ethers6m
- Naming Epoxides18m
- Naming Thiols11m
- Alcohol Synthesis7m
- Leaving Group Conversions - Using HX11m
- Leaving Group Conversions - SOCl2 and PBr313m
- Leaving Group Conversions - Sulfonyl Chlorides7m
- Leaving Group Conversions Summary4m
- Williamson Ether Synthesis3m
- Making Ethers - Alkoxymercuration4m
- Making Ethers - Alcohol Condensation4m
- Making Ethers - Acid-Catalyzed Alkoxylation4m
- Making Ethers - Cumulative Practice10m
- Ether Cleavage8m
- Alcohol Protecting Groups3m
- t-Butyl Ether Protecting Groups5m
- Silyl Ether Protecting Groups10m
- Sharpless Epoxidation9m
- Thiol Reactions6m
- Sulfide Oxidation4m
- 13. Alcohols and Carbonyl Compounds2h 17m
- 14. Synthetic Techniques1h 26m
- 15. Analytical Techniques:IR, NMR, Mass Spect6h 50m
- Purpose of Analytical Techniques5m
- Infrared Spectroscopy16m
- Infrared Spectroscopy Table31m
- IR Spect:Drawing Spectra40m
- IR Spect:Extra Practice26m
- NMR Spectroscopy10m
- 1H NMR:Number of Signals26m
- 1H NMR:Q-Test26m
- 1H NMR:E/Z Diastereoisomerism8m
- H NMR Table21m
- 1H NMR:Spin-Splitting (N + 1) Rule17m
- 1H NMR:Spin-Splitting Simple Tree Diagrams11m
- 1H NMR:Spin-Splitting Complex Tree Diagrams8m
- 1H NMR:Spin-Splitting Patterns8m
- NMR Integration18m
- NMR Practice14m
- Carbon NMR4m
- Structure Determination without Mass Spect47m
- Mass Spectrometry12m
- Mass Spect:Fragmentation28m
- Mass Spect:Isotopes27m
- 16. Conjugated Systems6h 13m
- Conjugation Chemistry13m
- Stability of Conjugated Intermediates4m
- Allylic Halogenation12m
- Reactions at the Allylic Position39m
- Conjugated Hydrohalogenation (1,2 vs 1,4 addition)26m
- Diels-Alder Reaction9m
- Diels-Alder Forming Bridged Products11m
- Diels-Alder Retrosynthesis8m
- Molecular Orbital Theory9m
- Drawing Atomic Orbitals6m
- Drawing Molecular Orbitals17m
- HOMO LUMO4m
- Orbital Diagram:3-atoms- Allylic Ions13m
- Orbital Diagram:4-atoms- 1,3-butadiene11m
- Orbital Diagram:5-atoms- Allylic Ions10m
- Orbital Diagram:6-atoms- 1,3,5-hexatriene13m
- Orbital Diagram:Excited States4m
- Pericyclic Reaction10m
- Thermal Cycloaddition Reactions26m
- Photochemical Cycloaddition Reactions26m
- Thermal Electrocyclic Reactions14m
- Photochemical Electrocyclic Reactions10m
- Cumulative Electrocyclic Problems25m
- Sigmatropic Rearrangement17m
- Cope Rearrangement9m
- Claisen Rearrangement15m
- 17. Ultraviolet Spectroscopy51m
- 18. Aromaticity2h 31m
- 19. Reactions of Aromatics: EAS and Beyond5h 1m
- Electrophilic Aromatic Substitution9m
- Benzene Reactions11m
- EAS:Halogenation Mechanism6m
- EAS:Nitration Mechanism9m
- EAS:Friedel-Crafts Alkylation Mechanism6m
- EAS:Friedel-Crafts Acylation Mechanism5m
- EAS:Any Carbocation Mechanism7m
- Electron Withdrawing Groups22m
- EAS:Ortho vs. Para Positions4m
- Acylation of Aniline9m
- Limitations of Friedel-Crafts Alkyation19m
- Advantages of Friedel-Crafts Acylation6m
- Blocking Groups - Sulfonic Acid12m
- EAS:Synergistic and Competitive Groups13m
- Side-Chain Halogenation6m
- Side-Chain Oxidation4m
- Reactions at Benzylic Positions31m
- Birch Reduction10m
- EAS:Sequence Groups4m
- EAS:Retrosynthesis29m
- Diazo Replacement Reactions6m
- Diazo Sequence Groups5m
- Diazo Retrosynthesis13m
- Nucleophilic Aromatic Substitution28m
- Benzyne16m
- 20. Phenols55m
- 21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
- Naming Aldehydes8m
- Naming Ketones7m
- Oxidizing and Reducing Agents9m
- Oxidation of Alcohols28m
- Ozonolysis7m
- DIBAL5m
- Alkyne Hydration9m
- Nucleophilic Addition8m
- Cyanohydrin11m
- Organometallics on Ketones19m
- Overview of Nucleophilic Addition of Solvents13m
- Hydrates6m
- Hemiacetal9m
- Acetal12m
- Acetal Protecting Group16m
- Thioacetal6m
- Imine vs Enamine15m
- Addition of Amine Derivatives5m
- Wolff Kishner Reduction7m
- Baeyer-Villiger Oxidation39m
- Acid Chloride to Ketone7m
- Nitrile to Ketone9m
- Wittig Reaction18m
- Ketone and Aldehyde Synthesis Reactions14m
- 22. Carboxylic Acid Derivatives: NAS2h 51m
- Carboxylic Acid Derivatives7m
- Naming Carboxylic Acids9m
- Diacid Nomenclature6m
- Naming Esters5m
- Naming Nitriles3m
- Acid Chloride Nomenclature5m
- Naming Anhydrides7m
- Naming Amides5m
- Nucleophilic Acyl Substitution18m
- Carboxylic Acid to Acid Chloride6m
- Fischer Esterification5m
- Acid-Catalyzed Ester Hydrolysis4m
- Saponification3m
- Transesterification5m
- Lactones, Lactams and Cyclization Reactions10m
- Carboxylation5m
- Decarboxylation Mechanism14m
- Review of Nitriles46m
- 23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
- 24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
- Tautomerization9m
- Tautomers of Dicarbonyl Compounds6m
- Enolate4m
- Acid-Catalyzed Alpha-Halogentation4m
- Base-Catalyzed Alpha-Halogentation3m
- Haloform Reaction8m
- Hell-Volhard-Zelinski Reaction3m
- Overview of Alpha-Alkylations and Acylations5m
- Enolate Alkylation and Acylation12m
- Enamine Alkylation and Acylation16m
- Beta-Dicarbonyl Synthesis Pathway7m
- Acetoacetic Ester Synthesis13m
- Malonic Ester Synthesis15m
- 25. Condensation Chemistry2h 9m
- 26. Amines1h 43m
- 27. Heterocycles2h 0m
- Nomenclature of Heterocycles15m
- Acid-Base Properties of Nitrogen Heterocycles10m
- Reactions of Pyrrole, Furan, and Thiophene13m
- Directing Effects in Substituted Pyrroles, Furans, and Thiophenes16m
- Addition Reactions of Furan8m
- EAS Reactions of Pyridine17m
- SNAr Reactions of Pyridine18m
- Side-Chain Reactions of Substituted Pyridines20m
- 28. Carbohydrates5h 53m
- Monosaccharide20m
- Monosaccharides - D and L Isomerism9m
- Monosaccharides - Drawing Fischer Projections18m
- Monosaccharides - Common Structures6m
- Monosaccharides - Forming Cyclic Hemiacetals12m
- Monosaccharides - Cyclization18m
- Monosaccharides - Haworth Projections13m
- Mutarotation11m
- Epimerization9m
- Monosaccharides - Aldose-Ketose Rearrangement8m
- Monosaccharides - Alkylation10m
- Monosaccharides - Acylation7m
- Glycoside6m
- Monosaccharides - N-Glycosides18m
- Monosaccharides - Reduction (Alditols)12m
- Monosaccharides - Weak Oxidation (Aldonic Acid)7m
- Reducing Sugars23m
- Monosaccharides - Strong Oxidation (Aldaric Acid)11m
- Monosaccharides - Oxidative Cleavage27m
- Monosaccharides - Osazones10m
- Monosaccharides - Kiliani-Fischer23m
- Monosaccharides - Wohl Degradation12m
- Monosaccharides - Ruff Degradation12m
- Disaccharide30m
- Polysaccharide11m
- 29. Amino Acids3h 20m
- Proteins and Amino Acids19m
- L and D Amino Acids14m
- Polar Amino Acids14m
- Amino Acid Chart18m
- Acid-Base Properties of Amino Acids33m
- Isoelectric Point14m
- Amino Acid Synthesis: HVZ Method12m
- Synthesis of Amino Acids: Acetamidomalonic Ester Synthesis16m
- Synthesis of Amino Acids: N-Phthalimidomalonic Ester Synthesis13m
- Synthesis of Amino Acids: Strecker Synthesis13m
- Reactions of Amino Acids: Esterification7m
- Reactions of Amino Acids: Acylation3m
- Reactions of Amino Acids: Hydrogenolysis6m
- Reactions of Amino Acids: Nihydrin Test11m
- 32. Lipids 2h 50m
- 34. Nucleic Acids1h 32m
- 35. Transition Metals5h 33m
- Electron Configuration of Elements45m
- Coordination Complexes20m
- Ligands24m
- Electron Counting10m
- The 18 and 16 Electron Rule13m
- Cross-Coupling General Reactions40m
- Heck Reaction40m
- Stille Reaction13m
- Suzuki Reaction25m
- Sonogashira Coupling Reaction17m
- Fukuyama Coupling Reaction15m
- Kumada Coupling Reaction13m
- Negishi Coupling Reaction16m
- Buchwald-Hartwig Amination Reaction19m
- Eglinton Reaction17m
Drawing Newman Projections - Online Tutor, Practice Problems & Exam Prep
To analyze a condensed structure, convert it to a bond line structure, focusing on the bond of interest, such as C2-C3. Visualize the bond using a Newman projection, adding implied hydrogens only around the bond of interest. Draw the front and back carbons with their respective groups, ensuring to identify the most stable conformation, typically the anti conformation with a dihedral angle of 180 degrees. This method aids in understanding conformational analysis and stability in organic compounds.
As we learned already, we use Newman projections to visualize the rotations of conformers. Now we will learn the steps involved to draw the perfect one.
Introduction to Drawing Newman Projections
Video transcript
Six Steps to Drawing Newman Projections
Worked Example:Draw the most energetically favorable Newman Projection for CH3CH2CH2CH2CH3 down the C2 – C3 bond.
1. Convert problem into bondline structure
Step 1 to Drawing Newman Projections
Video transcript
The first thing that I always do is, if you're given a condensed structure, which is often the case, you need to convert the problem into a bond-line structure. Okay? So what that means is that I want to take this 5 Carbon chain, or whatever I'm given, and turn it into bond line. So that's the first thing I'm going to do. Five carbons right there. So, this is pentane.
2. Highlight the bond of interest
Step 2 to Drawing Newman Projections
Video transcript
The second thing I'm going to do is I'm going to highlight the bond of interest. What is the bond of interest? What? It's this, C2C3. That's your professor telling you that he wants you to focus on a certain bond that's going to rotate. Okay? Just like when I was talking to you about conformers that you could have sigma with S cis or S trans, he's picking out which sigma bond you're going to use, which sigma bond you're going to rotate. That's going to be this sigma bond right there. Because basically, what you want to do is you want to go from the second carbon to the third carbon. That's what C2C3 means. C2C3. Alright? Now, it could have also been this one, just letting you know, it could have also been this one because if you were counting your one from over here, then this would have been your 2 and your 3. Okay? But I'll just go ahead and use this other one. So this is my 2, this is my 3. Perfect. So, I highlighted the bond of interest. You don't need to necessarily write the numbers as long as you just know which bond it is.
3. Draw an eyeball glaring down the length of the bond
Step 3 to Drawing Newman Projections
Video transcript
What we want to do is, this part sounds silly, I'm going to redraw this, but I actually want you to do the eyeball thing. I want you to draw an eyeball looking down the length of that bond. Okay? So, I want you to draw an eyeball and make it look straight at that carbon. Okay, so pretend that's you, squinting your eyes at it and you're going to try to figure out what this thing is going to look like if I was looking straight at it.
4. Surround only the bond of interest with ALL implied hydrogens
Step 4 to Drawing Newman Projections
Video transcript
Now the way you're going to do that is that you surround only the bond of interest with all implied hydrogens. That means if there's any implied hydrogens on that carbon or on that carbon, I need to add them. Okay? How about the hydrogens on that carbon? Do I add those as well? No, because that's not the bond of interest. The bond of interest is only going to be from 2 to 3. So what that means is I'm going to add 2 H's here and I'm also going to add 2 H's here. Okay? But I'm not going to add H's anywhere else because that's not the bond of interest.
5. Draw a front carbon with 3 groups in the front and a back carbon with 3 groups in the back
Step 5 to Drawing Newman Projections
Video transcript
Now what we're going to do is we're going to draw a front carbon with 3 groups in the front and then a back carbon with 3 groups in the back like I was doing when I told you guys about the way the Newman Projection works. So I'm going to say that, for example, little dot. Okay little dot. Okay? And I would draw that it has 3 things coming off of it. Okay? You can draw your little triangle thing or whatever that's called, however you want. You can start with it with a point up or you can start with a point down. It doesn't matter as long as the other one is consistent. So basically, what I would say is then, okay, what are the three things that that red carbon is attached to? Well, it seems to be attached to an H on the top, an H on the top, and then a CH3 at the bottom. That is this CH3 right here. Get that? Then I look back at the blue one. The blue one, imagine that it's kind of peeking out from behind the red one. So the blue one is going to be a circle behind and then I'm going to draw the 3 groups that the blue one has. So the blue one has what? It seems to have 2 H's, H and H. And then what else does it have? Well, it has a 2 carbon chain coming off of it. So that would be what you could just write as CH2CH3. Does that make sense? Okay? Another way to write that would have been to write ET, which stands for Ethyl. Okay? Another way to write CH3 would be to write ME, which stands for Methyl. Okay? And there are abbreviations for a bunch of these different ones. Alright. And your professor might use those more than he actually uses the letters.
6. Determine which dihedral angle would correspond
Step 6 to Drawing Newman Projections
Video transcript
So now that we've drawn that Newman projection, that is a valid Newman projection. That could be right. The only thing is that I don't know if it's the energy state that the professor was asking for because the professor could ask for any energy state. He could ask for anti. He could ask for gauche. He could ask for eclipse. Maybe even something in the middle. So I have to make sure that this is the exact one that he wants. Okay? So then to determine which dihedral angle would correspond, I have to go up here and see what he said. Well, he specifically said to draw the most energetically favorable. What does energetically stable mean? Stable. Okay? So we're looking for the most stable conformation. What is the most stable conformation? That's going to be anti. Remember, anti is the most stable. So let's go down and see if that's what I drew. And what's the bond dihedral angle, by the way, for anti? 180°. Let's go down and see if that's what I drew. What I have is a large group in the back and a large group in the front. They appear to be 180° degrees away from each other, so this would be anti. So this would be your right answer, and this would be what would get you the points on the exam. Okay? So even if I drew the wrong conformation at the beginning, you could still rotate it into the right conformation. The important part is that you're following all of these steps.
Hint:This question asked for the most energetically favorable = most stable. Which conformation is most stable?
The right answer was anti. You got it. So it turns out this time we drew it correctly on the first try. But there will be other examples where we will have to rotate the Newman Projection into the correct position.
Draw the most energetic Newman Projection of CH3CH(C6H5)CH3
Hint:Not all Newman Projections can form an anti, gauche and eclipsed conformation. If you have no clear large group on one side of the projection, you’ll just be stuck with projections called staggered (not overlapping) and eclipsed (overlapping).
Draw the most stable Newman Projection of CH3CH2 CH2OH through the C2 – C1 bond.
Do you want more practice?
More setsHere’s what students ask on this topic:
How do you convert a condensed structure to a bond line structure for Newman projections?
To convert a condensed structure to a bond line structure, follow these steps: Identify the carbon chain and draw it as a zigzag line, where each vertex represents a carbon atom. Add any substituents or functional groups to the appropriate carbons. For example, a condensed structure like CH3CH2CH2CH3 would be drawn as a four-carbon zigzag line. This conversion helps in visualizing the molecule more clearly for Newman projections.
What is the bond of interest in a Newman projection and how do you identify it?
The bond of interest in a Newman projection is the specific sigma bond you are analyzing for rotation. To identify it, look for the bond specified in the problem, often denoted by the carbons it connects, such as C2-C3. Highlight this bond in your bond line structure, as it will be the axis around which you visualize the molecule in the Newman projection.
How do you draw the front and back carbons in a Newman projection?
In a Newman projection, the front carbon is represented by a dot, and the back carbon is represented by a circle. From the dot, draw three lines representing the bonds to the front carbon's substituents. From the circle, draw three lines representing the bonds to the back carbon's substituents. Ensure the groups are positioned correctly to reflect the molecule's 3D structure.
What is the most stable conformation in a Newman projection and how do you identify it?
The most stable conformation in a Newman projection is typically the anti conformation, where the largest groups on the front and back carbons are 180 degrees apart. This minimizes steric hindrance. To identify it, look for a dihedral angle of 180 degrees between the largest groups. This conformation is energetically favorable due to reduced repulsion between bulky groups.
How do you determine the dihedral angle in a Newman projection?
The dihedral angle in a Newman projection is the angle between two substituents on adjacent carbons. To determine it, visualize the molecule from the perspective of the bond of interest. Measure the angle between the substituents on the front and back carbons. Common angles are 0 degrees (eclipsed), 60 degrees (gauche), and 180 degrees (anti).
Your Organic Chemistry tutors
- Use a Newman projection about the indicated bond to draw the most stable conformer for each compound. a. 3-me...
- Use a Newman projection about the indicated bond to draw the most stable conformer for each compound. b. 3,3-...
- Convert each Newman projection to the equivalent line–angle formula, and assign the IUPAC name. g. h.
- Convert each Newman projection to the equivalent line–angle formula, and assign the IUPAC name. a. b.
- Draw a Newman projection, similar to [FIGURE 3-25} down the C1—C6 bond in the equatorial conformation of met...
- Draw Newman projections of the following molecules viewed from the direction of the blue arrows. b.
- b. Draw a potential-energy diagram for rotation about the C-2-C-3 bond of pentane through 360°, starting with ...
- For rotation about the C-3-C-4 bond of 2-methylhexane, do the following: a. Draw the Newman projection of the ...
- c. Draw Newman projections of the two conformers of the trans isomer. d. Which of the conformers predominates ...
- (••) Given the following structures, show the Newman projection that would result from looking down the indica...
- (••) Given the following structures, show the Newman projection that would result from looking down the indica...
- Using the Newman projections shown, draw each molecule in its line-angle drawing with all hydrogens and substi...
- Using the Newman projections shown, draw each molecule in its line-angle drawing with all hydrogens and substi...
- (•) Given the first Newman projection and the direction and degree of rotation, fill in the resulting Newman p...
- (•) Given the first Newman projection and the direction and degree of rotation, fill in the resulting Newman p...
- (•) Given the first Newman projection and the direction and degree of rotation, fill in the resulting Newman p...
- (•) Given the first Newman projection and the direction and degree of rotation, fill in the resulting Newman p...
- (••) Given the following structures, show the Newman projection that would result from looking down the indica...
- (••) Given the following structures, show the Newman projection that would result from looking down the indica...
- Draw Newman projections along the C3―C4 bond to show the most stable and least stable conformations of 3-ethy...
- For each molecule, draw the Newman projection you would observe if you looked down the Cₐ - Cᵦ bond in the dir...
- (••) Given the following structures, show the Newman projection that would result from looking down the indica...
- (•••) Looking down the indicated bond, show the three most stable conformations and choose the one that is mos...
- (••) For each of the following structures, which staggered Newman projection skeleton from Assessment 3.51 sho...
- Is each of the following a cis isomer or a trans isomer?d. <IMAGE>e. <IMAGE>f. <IMAGE>
- Convert each Newman projection to the equivalent line–angle formula, and assign the IUPAC name.c. <IMAGE>...
- Using Newman projections, draw the most stable conformer for each of the following:c. 3,3-dimethylhexane, view...
- For the following molecule, draw the Newman projection (around the 2,3-bond) with a dihedral angle of 180° bet...
- Conformational studies on ethane-1,2-diol (HOCH2—CH2OH) have shown the most stable conformation about the cen...
- b. Draw the conformer that is present in greatest concentration.