In general a carbon chain with 3 carbons or less with a nitrogen or oxygen is soluble in water. If 4 carbons it's borderline. Anything beyond that is not very soluble.What are the solubility rules when you have Nitrogen on Carbon chain?
It is sparingly soluble in water (6.9 g/100 mL). As I stated,,,,,,when you hit the " magic " number of 4,,,,,water solubility begins to decrease and Van Der Waals forces DOMINATE hydrogen bonding. For the past 35 years, I was always most successful using THF......this cyclic ether is also 4 carbons...BUT......the carbons are " pulled back " due to the cyclic structure....and dissolves wonderfully with water !!!! With branching or in a cyclic structure, hydrogen bonding is able to compete more effectively against the Van Der Waals forces.Why is diethyl ether not soluble in water? It was lone pairs on the oxygen doesn't it? Thanks!