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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Watkin on September 02, 2009, 01:44:23 AM

Title: Fischer projection of the free acid form of naproxen
Post by: Watkin on September 02, 2009, 01:44:23 AM

What does the fischer projection of the free acid of naproxen look like?

So far I am only familiar with drawing fischer diagrams of small monosaccharides and I have absolutely no idea how to draw a molecule of such complexity.

Any help would be appreciated.

Thanks

Title: Re: Fischer projection of the free acid form of naproxen
Post by: azmanam on September 02, 2009, 06:01:44 AM

Fisher projections are uncommon for molecules other than sugars, but I suppose you could do it for the single stereocenter if you want.  see the image on the wikipedia page for projecting a tetrahedron onto a Fischer projection.  See if you can give it a guess and post it here.

http://en.wikipedia.org/wiki/Fischer_projection

Title: Re: Fischer projection of the free acid form of naproxen
Post by: Dan on September 02, 2009, 06:32:10 AM

Quote from: Watkin on September 02, 2009, 01:44:23 AM

So far I am only familiar with drawing fischer diagrams of small monosaccharides and I have absolutely no idea how to draw a molecule of such complexity.

The theory is exactly the same as with monosaccharides, but in this case there is only one stereocentre. With only one stereocentre the Fischer projection of naproxen is actually far simpler than that of a sugar - think about the Fischer projections of glyceraldehyde (which also only has one stereocentre).

Title: Re: Fischer projection of the free acid form of naproxen
Post by: Watkin on September 05, 2009, 10:39:12 PM

Would it look something similar to the attachment I added?

Title: Re: Fischer projection of the free acid form of naproxen
Post by: Dan on September 07, 2009, 05:27:18 AM

Right idea, I disagree with the stereochemistry though...