How can I draw Fischer projections from wedge and dash?

1 Answer
Oct 29, 2014

Answer:

Here's how I do it.

Explanation:

We must view a wedge-dash formula from the correct angle to convert it to a Fischer projection.

Here's the wedge-dash structure.

upload.wikimedia.org

We now view the molecule with #"C-1"# at the top and with all chiral carbons closest to our eye.

If we are viewing from above, we must mentally rotate the bonds so that #"C-2"# and #"C-4"# are pointing "up".

When we do this, the wedges become dashes, and the dashes become wedges, as in the picture below.

Glucose

So the #"OH"# groups on #"C-2"# and #"C-4"# become wedges.

We don't rotate #"C-3"# and #"C-5"#, so the bonds to the #"OH"# groups on those atoms remain the same.

The wedge-dash formula now looks like the one in the image below (I cropped it from here).

Fischer

The wedges are now on the right, and the dashes are on the left.

It is as if we had wrapped the chain around a cylindrical tube.

When you flatten the structure onto the surface of the cylinder, you get the Fischer projection of D-glucose.

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