I wonder how chemists worked out the structures of organic molecules before spectroscopy (especially NMR) was invented?
Surely, we could do functional group tests, but the correct connection of atoms and function groups would be hard to tell when the number of carbon atoms get larger. E.g. How could they tell one compound was 2-hexanol rather than 3-hexanol? How could Emil Fischer and others worked out the correct structures of carbohydrates with so many chiral centers? And god forbids, how could the chemists worked out the correct structures of natural products with fused rings (eg the cholesterol family)? It's not a trivial task even with 2D NMR!
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