8_man

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If theres hydrogens on the nitrogen, its generally soluble.

Tertiary amines are somewhat soluble (limited to really short C-chain compounds).

(not exactly sure what you want to know beyond this but lemme know)
 

orgoman22

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What are the solubility rules when you have Nitrogen on Carbon chain?
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.

Hope this helps.

Dr. Romano
 
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fit2

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Why is diethyl ether not soluble in water? It was lone pairs on the oxygen doesn't it? Thanks!
 

orgoman22

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Why is diethyl ether not soluble in water? It was lone pairs on the oxygen doesn't it? Thanks!
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.

I hope this helps

Dr. Romano
 

fit2

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Alright. Thank you very much for the help! I'llkeep number 4 in my mind ;)
 
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IranBrooklyn77

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Just to be clear if we do comparison between Ethanol and pentanol than Ethanol would be more water soluble? Is that correct