THF and water

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hydrogen bond with oxygen on THF. And there are different geometries surrounding the carbon atoms bound to the oxygen in THF vs. diethyl ether.

diethyl ether chain can rotate freely but THF can not. So THF has strong interaction with water. It is like bending the two O-C bonds to expose oxygen and make it easy for hydrogen bond to form in THF.
 
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hydrogen bond with oxygen on THF. And there are different geometries surrounding the carbon atoms bound to the oxygen in THF vs. diethyl ether.

diethyl ether chain can rotate freely but THF can not. So THF has strong interaction with water. It is like bending the two O-C bonds to expose oxygen and make it easy for hydrogen bond to form in THF.

two things, you asked a really good question and this is (IMO) a really good answer. That took me like 3 hours to figure out. lol 🙂 But seriously, all of you UCSD students are pretty smart.
 
This can also be explained in terms of kinetics in combination with intermolecular forces and sterics.

Intermolecular forces are attractive forces that develop when two charges (including partially charged molecules) at a specific time , t, approach each other at some distance, r. Understanding this, and the dynamic nature of molecules, the H2O molecules have a higher chance of approaching the oxygen in THF because it is sterically restricted from rotating its adjacent carbon bonds. This therefore allows a higher probability for "hydrogen bonding" to occur.

In summary, the reason why THF can dissolve in H20 better than di-ethyl either because it has a higher probability to "hydrogen bond" more often at a specific time t, when compared to diethyl ether. It's really important to ask the question what is more likely to occur more often ( hence the relation to kinetics) rather than assume some black or white picture. Understanding that molecules and everything in life is DYNAMIC is the key to understanding chemistry =).
 
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