Ch. 4 - Alkanes and CycloalkanesWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

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. 

Example #1: Introduction to Drawing Newman Projections

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

Concept #1: Step 1

2. Highlight the bond of interest

Concept #2: Step 2

3. Draw an eyeball glaring down the length of the bond

Concept #3: Step 3

4. Surround only the bond of interest with ALL implied hydrogens

Concept #4: Step 4

5. Draw a front carbon with 3 groups in the front and a back carbon with 3 groups in the back

Concept #5: Step 5

6. Determine which dihedral angle would correspond

Concept #6: Step 6

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. 

Practice: 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).

Practice: Draw the most stable Newman Projection of CH3CH2 CH2OH through the C2 – C1 bond. 

Additional Problems
Write a structural formula for the most stable conformation of each of the following compounds:  (a)  2,2,5,5-Tetramethylhexane (Newman projection of conformation about C-3—C-4 bond) 
Draw the lowest and the highest energy Newman Projection looking down the C1-C2 bond for 1-bromo-2-methylpropane.
Name the following molecule. 
Draw a Newman projection for the following compound as viewed down the indicated bond.
Use a Newman projection to draw the most stable conformation of 3-methylpentane, looking down the C2—C3 bond.  
For the line angle drawing: give the IUPAC name for the compound AND draw the most stable Newman projection, looking down the bond indicated with the thick line. (E.G. the first compound, draw the Newman projection looking down the #1 C. The circle of the Newman projection represents the C facing us.)
For the line angle drawing: give the IUPAC name for the compound AND draw the most stable Newman projection, looking down the bond indicated with the thick line. (E.G. the first compound, draw the Newman projection looking down the #1 C. The circle of the Newman projection represents the C facing us.)
For the line angle drawing: give the IUPAC name for the compound AND draw the most stable Newman projection, looking down the bond indicated with the thick line. (E.G. the first compound, draw the Newman projection looking down the #1 C. The circle of the Newman projection represents the C facing us.)
For the line angle drawing: give the IUPAC name for the compound AND draw the most stable Newman projection, looking down the bond indicated with the thick line. (E.G. the first compound, draw the Newman projection looking down the #1 C. The circle of the Newman projection represents the C facing us.)
For the line angle drawing: give the IUPAC name for the compound AND draw the most stable Newman projection, looking down the bond indicated with the thick line. (E.G. the first compound, draw the Newman projection looking down the #1 C. The circle of the Newman projection represents the C facing us.)
One possible stereoisomer of 2-bromopentane is pictured below. Assuming that sterically a CH3 is bigger than a Br, provide the following: a. A sawhorse representation, with C2 in the front and C3 in the back, with the Br on C2 and the CH2CH3 on C3 pointing UP. b. The Newman projection of the most stable conformer of this molecule with the CH2CH3 on C3 pointing UP on the back carbon. c. The Newman projection of the least stable conformer of this molecule with the CH2CH3 on C3 pointing UP on the back carbon. d. The Newman projection having the Br and Ha antiperiplanar. e. The sawhorse representation of what you drew in d.
Draw a Newman projection of the following compound as viewed from the angle indicated:
Assume a methyl group is larger than a chloro group and draw the lowest energy conformation of 2-chlorohexane as a Newman projection viewed down the C2-C3 bond. Use the alkyl group abbreviations Me, Et, Pr, etc for the alkyl substituents on C2 and C3.
The conformations of (+)-epichlorohydrin (1), viewed along the Ca—Cb bond, can be analyzed in exactly the same manner as the acyclic alkanes discussed in Chapter 4 (J. Phys. Chem. A 2000, 104, 6189–6196). (a) Draw all staggered conformations for 1 viewed along this bond.
Find the correct Newman projection of Molecule A from C3 to C4.  
Using the numbering from your IUPAC name for the following molecule (ketone group has the priority), find the correct the Newman projection from C3 to C4.  
Consider (1R, 3R)-1,3-dimethylcyclohexane. Draw its Newman projection. Paying attention to stereochemistry, draw an acceptable regular 3D structure.
Provide the Newman projection of the following compound
Provide a structural formula for the compound below. Be sure to identify stereoisomers properly. Viewing down the C3-C4 bond of 3,4-dimethylhexane, give a sawhorse formula for the highest energy conformation
On the template provided, draw the Newman projection for the most stable conformation of the molecule shown. Draw the Newman viewing from Carbon #3 to Carbon #2 (IUPAC numbering). The hydrogen on carbon #3 has been added to get you started.
Draw the lowest and the highest energy Newman projections for 2,3- dimethylbutane looking down the C2-C3 bond.
Sight down the C-2—C-3 bond, and draw Newman projection formulas for the  (a) Most stable conformation of 2,2-dimethylbutane
Draw the Newman projection through C1-C2 for the least stable conformation of 2-methyl-1-butanol.
Convert each of the following to a Newman Projection along the C2-C3 bond
When looking down the assigned arrow, draw the Newman projection formula for this molecule:
When looking down the assigned arrow, draw the Newman projection formula for this molecule:
Draw Newman projections of the following molecule in the conformations shown from the direction indicated. Label the lower energy conformer
(b) Draw the Newman projection in the conformation drawn from the perspective shown below.
Translate the given conformer from the wedge-and-dash drawing into its Newman projection. (Hint: first decide whether the confirmation is staggered or eclipsed)
Consider the molecule drawn below. Draw the Newman projection of the molecule as drawn above, looking down the C2-C3 bond.
Consider the molecule drawn below. Draw the Newman projection where the halogens are eclipsed. 
Consider the molecule drawn below. Draw the Newman projection where the halogens are anti.
Translate the given theoretical conformer from the wedge-and-dash drawing into its Newman projection.
Translate the given conformer from the wedge-and-dash drawing into its Newman projection. 
Translate the given conformer from the wedge and dash drawing into its Newman projection.
Translate the given conformer from the wedge-and-dash drawing into its Newman projection.
Which of the following is a Newman projection for the following compound as viewed down the indicated bond in the conformation shown?