Merdan
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I have 3 questions; 1) Place the following amines in order of basicity, starting with the most basic: Ethylamine, Diethylamine, Diethylpropylamine, Phenylamine. I assume the idea is that the most stable amine or the one with highest b.p. will be most basic? In this case phenylamine be most basic? 2) What would you expect to happen if phenylamine reacted with concentrated sulphuric acid and tin, and then reacted with sodium hydroxide? Here nitrobenzene does react with hcl/sn to give the amine anyway idk if its a reversible but why would you further reduce it anyway. 3) Does anyone have a good way of remembering the chain of reactions of making amines from haloalkane + ammonia also chain reactions of making the salts of amines where haloalkane + primary amine. I am struggling with remembering those chain reactions so I guess will forget if I don't get a systematic way to remember so if anyone has answers pls share thanks...
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username913907
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(Original post by Merdan)
I have 3 questions; 1) Place the following amines in order of basicity, starting with the most basic: Ethylamine, Diethylamine, Diethylpropylamine, Phenylamine. I assume the idea is that the most stable amine or the one with highest b.p. will be most basic? In this case phenylamine be most basic? 2) What would you expect to happen if phenylamine reacted with concentrated sulphuric acid and tin, and then reacted with sodium hydroxide? Here nitrobenzene does react with hcl/sn to give the amine anyway idk if its a reversible but why would you further reduce it anyway. 3) Does anyone have a good way of remembering the chain of reactions of making amines from haloalkane + ammonia also chain reactions of making the salts of amines where haloalkane + primary amine. I am struggling with remembering those chain reactions so I guess will forget if I don't get a systematic way to remember so if anyone has answers pls share thanks...
b.p has no relation to basicity.

The basicity of amines is related to the availability/energy of the N lone pair. Electron donating groups increase the energy of the lone pair and make it more basic. Conversely electron withdrawing groups reduce the basicity as the lone pair in conjugated into the pi system for pi acceptors lowering the energy. Or for inductive withdrawing groups this lowers the energy of the one pair by withdrawing electron density off the N atom.
Now you should be able to put together a good answer!!! One clue for if you didn't know..... Alkyl groups are weak donating groups.
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