How to Draw a Newman Projection in Organic Chemistry

The following instruction set will help an individual learn how to draw a Newman projection in organic chemistry. While organic chemistry knowledge and experience is not necessary to complete the instruction set, it is helpful.

Part 1
Part 1 of 3:

Basic Molecular Drawing

  1. 1
    Learn basic molecular drawing techniques.
    • If already familiar with drawing molecules, proceed to Part 2: "3-Dimensional Structure of Organic Molecules."
  2. 2
    Consider the name. Review IUPAC molecule naming at Name a Hydrocarbon Chain Using the IUPAC Method and identify the molecule being studied.
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  3. 3
    Count the number of carbon atoms. This will be denoted by using the prefix on the name of the chemical, see the list below.
    • 1 carbon: Meth
    • 2 carbons: Eth
    • 3 carbons: Prop
    • 4 carbons: But
    • 5 carbons: Pent
    • 6 carbons: Hex
    • 7 carbons: Hept
    • 8 carbons: Oct
    • 9 carbons: Non
    • 10 carbons: Dec
    • Be sure to include hydrogens attached to the carbon atoms.
  5. Refer back to the IUPAC name to see where the inorganic groups are located.
    • Examples of inorganic side groups include -OH, -COOH, NH2, Cl, Br, etc.
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Part 2
Part 2 of 3:

3-Dimensional Structure of Organic Molecules

  1. 1
    Learn basics of stereochemistry.
    • If already familiar with stereochemistry, proceed to Part 3: "Drawing a Newman Projection."
  2. A stereocenter is a carbon atom that has four different groups/atoms attached to it and contains 3-Dimensional characteristics (wedge and dash).
    • A wedged line means the atom is coming "out of the plane" or towards you. A dashed line means the atom is going "into the plane" or away from you.
    • Each side group on the stereocenter can be on a wedge or a dash.
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Part 3
Part 3 of 3:

Drawing a Newman Projection

  1. A Newman Projection focuses on one specific bond of the molecule, and note which atoms are attached to these carbon atoms. Add an eye with an arrow looking down the carbon-carbon bond being studied.
    • Example: 2-3 means looking down the carbon 2 and carbon 3 bond. Notice how the two hydrogens have 3-Dimensional structure. While not a stereocenter, drawing the hydrogens in this way makes drawing the Newman Projection much easier.
  2. Note: molecule being drawn in the Newman Projection is 2-butanol.
  4. Look at the 3-Dimensional Drawing from above and label which atoms are attached to this carbon and where each is located.
    • Atoms on a wedge point right
    • Atoms on a dash point left
    • Atoms in the plane of the molecule go up or down.
  5. Look at the 3-Dimensional Drawing from above and label which atoms are attached to this carbon and where each is located.
    • Note the 3-Dimensional location of all the atoms from the structure above and check to make sure the Newman Projection matches for each.
  6. Each 60 degree turn of the atoms creates a new conformation, and there are six total conformations for each Newman Projection.
    • Staggered is most stable, eclipsed is least stable.
    • Completing the other three conformations is done in a similar way, with 60 degree rotations done for each.
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  • Question
    How can we find which Newman projection is more stable?
    Raff
    Community Answer
    The Newman structure of a molecule with the less steric strain is going to be the most stable. This will be essentially true in terms of the steric strain of the larger groups on the structure. Therefore, staggered structures are more stable than eclipsed structures; essentially, it gives the bigger groups more space from each other. Of the staggered structures, the anti conformer will be the most stable because the large groups are in a position where they are as far away from each other as possible.
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      Tips

      • Never try to draw the eclipsed conformation first. Drawing out the staggered form of the molecule first makes drawing the subsequent conformations easiest.
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      • If the molecule contains many carbons, make sure the number in the Newman Projection matches the number in the original molecule.
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