[vdemas]

Here's the question :

2-Hydroxeacetophenone is more volatile than 4-Hydroxyacetophenone.Discuss this observation in detail.


This is what I got :

I know their structures.
Can I say that  because the -OH and -COCH₃ groups in 2-hydroxyphenone is closer to each other than in 4-hyroxyacetophenone it is less stable than the latter and will therefore have a greater tendency to evaporate?

Please help.
I am using the Organic Chemistry textbook by  J G Smith ( 1st edition )and there is nothing in there about volatility.

[sjb]

It's a start, yes. However, in general the spatial orientation of groups has little to do with stability.

What is happening on a molecular level when something goes from liquid to gas?

[DrCMS]

Look up inter- and intra- molecular (hydrogen) bonding.

[nicolene]

Please help me because I have the same question and only got  as far as what you have on your post.

[ramboacid]

Volatility has to do with how well molecules tend to adhere to each other. If a liquid easily evaporates, then they intermolecular forces in the liquid must be easily able to be broken. If a liquid requires more energy input to evaporate, then the molecules in the liquid must have strong intermolecular interactions.

Intermolecular forces have to do with structures. Why would having the hydroxyl group at the opposite end of the ketone group allow for stronger intermolecular interactions than if the hydroxyl group was right next to the ketone group? Think about this spatially and which way would allow for more intermolecular hydrogen bonding. Also consider why the hydroxyl group at the 2 position might allow for intramolecular bonding.

[Babcock_Hall]

Try drawing how two or more 4-hydroxyacetophenone molecules would interact with each other in a liquid state.