I have the following question from my Organic Chemistry textbook:

I'm asked to convert the following line diagram into a Newman Projection.

enter image description here

The arrow pointing to the carbon signifies "looking down the carbon".

My logic was the following:

At the carbon that is being pointed at by the arrow, there are 3 bonds to other carbons, all of which are in the same plane due to the absence of any 'dashed lines' or 'solid wedges' that would indicate otherwise.

I then concluded that the geometry of that carbon is trigonal planar and that it has a lone pair, since all the bonds to other carbons are in the same plane.

However, drawing a Newman Projection for an atom with trigonal planar geometry proves to be impossible.

I'm not sure how to go about converting this line diagram into a Newman projection.

How can I do so?

Thank you.

  • $\begingroup$ You don't have a realistic structural formula to begin with. It should have had some wedge/dash information, but it is lost. $\endgroup$ Commented Oct 10, 2018 at 5:02
  • $\begingroup$ Your assumption about the geometry of the arrowed carbon is wrong: it isn't trigonal planar. In structure pictures like this you need to add missing hydrogens to give each carbon its normal compliment. $\endgroup$
    – matt_black
    Commented Oct 10, 2018 at 11:58

1 Answer 1


conversion of sawhorse and newnam projectionthis is how you can convert the str.s into each other. It should have had some wedge/dash or sawhorse information... for the conversion.


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