Converting Newman Fischer

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bchang57

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For any newman projections, is it SAFE to rotate either the front or back carbon so that the 2 methyl groups are eclipsed and then from there, draw the Fischer projection?

(Note: they aren't always methyl groups, they could be COOH, halides or something, but you get my point)

EDIT: I may have a revelation here!...

so after much staring and drawing and thinking.....I think I made a discovery that will help with this. Some verification would be nice 🙂

Here's my revelation:
When converting a newman to a fischer, the top carbon of a fischer projection is the carbon you are looking at infront of you. Or another way of stating that is the top carbon is the point of reference from where you begin and look down the line of carbons and their substituents. Therefore, if you were to draw the back carbon of the newman projection (the circle) as the top carbon in the fischer projection, you have to switch the sides the substituents are on in the newman projection to draw the fischer projection correctly. It's like taking the newmann projection, and rotating it on a horizontal plane so that now the back carbon (the circle) is in front and the front carbon (the dot) is in the back - they switched places.

Another interpretation of seeing this is if you keep the newman projection stationary and imagine yourself walking to the otherside (like looking at a work of art, and you decide to walk around to the other side of it to admire it) so that now you are looking at the back carbon, consequently, from your point of view, changing the back carbon to the front carbon now, and the front carbon has become the back carbon (now, you are standing on the side "into the page" and you are looking "out of the page" in terms of looking at the newman projection).
 
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or would anyone happen to be studying DAT Destroyer 2012 version?

Looking at problem 145 of the ochem section. Stuck on answer choice d) for R/S configuration

Edit: see above
 
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