2

Does anyone have any tips on how to approach these types of questions? A specific example would be:

Draw all constitutional isomers of $\ce{C2H4O}$

I can get the easier ones like vinyl alcohol, but it's hard to get ethylene oxide and it takes a long time for me to get acetaldehdye. And how would I know if I got all of the possible constitutional isomers?

John Snow
  • 4,515
  • 6
  • 29
  • 66

1 Answers1

5

I approach questions like this by considering all possibilities of arrangements of the non-hydrogen atoms. Obviously, there's C-C-O, C-O-C, and then the cyclic ethylene oxide.

Then I make sure I've matched bond orders to get the hydrogen count.

So I get vinyl alcohol, acetaldehyde, and ethylene oxide. H2C-O-CH2 would only work for a biradical, which is probably not expected.

The systematic fashion then is to arrange the "heavy" atoms, first in all linear forms, then all cyclic forms, then all two-ring forms, etc. Of course with large formulas, the number of isomers goes up exponentially.

Geoff Hutchison
  • 27,740
  • 3
  • 79
  • 145