Order of basicity and lipophilicity in organic compounds

[MrJason123]

Hello,

I want to rank the following compounds in order of basicity:
trimethylamine, tetramethylammonium chloride, 4-nitroaniline, aniline, acetanilide, 4-methylaniline.
I think this is the order, but I'm not sure for the last ones.
trimethylamine > 4-methylamine > aniline > 4-nitroaniline > tetramethylammonium chloride > acetanilide
Also what happens to their ionization and lipophilicity in pH=2 and pH=10?

And I want to rank these compounds in order of lipophilicity:
n-butanol, 2-butanol, butyl chloride, n-butyl acetate, butyl hydrogen sulphate

Can someone help me?

 

[berkeman]

Hello,

I want to rank the following compounds in order of basicity:
trimethylamine, tetramethylammonium chloride, 4-nitroaniline, aniline, acetanilide, 4-methylaniline.
I think this is the order, but I'm not sure for the last ones.
trimethylamine > 4-methylamine > aniline > 4-nitroaniline > tetramethylammonium chloride > acetanilide
Also what happens to their ionization and lipophilicity in pH=2 and pH=10?

And I want to rank these compounds in order of lipophilicity:
n-butanol, 2-butanol, butyl chloride, n-butyl acetate, butyl hydrogen sulphate

Can someone help me?

Welcome to the PF.

Is this for schoolwork?

 

[MrJason123]

No. I'm a student in University and I want to be sure about the answers in theses questions.

 

[berkeman]

Since it is for schoolwork, it needs to be posted in the Homework Help section of the PF, and you need to fill out the Homework Help Template that you are provided there. That includes the sections on the Relevant Equations/Concepts, and your Attempt at the Solution.

Please re-post in the Homework Help, Chemistry forum. Thank you.