Question

In the synthesis of aniline lab experiment, I have the following post-lab question which I do not know how to answer. Please help, be thorough, and please also describe any intermolecular forces at work. Thank you for your help and time.

"If NaOH was not added to the solution, and you then extracted with methylene chloride, what layer/phase would the product be found in? Why?"

Answer 1

if NaOH is not added, then the aniline will be present as "molecular" and not as "ionic"

note that

aniline in acidic media --> AnilineH+, has been protonated, then

this is soluble in water mostly

also note that if we add NAOH, we change the aniline from protonated +1, state to neutrla, 0 state

the aniline is organic, will be much more soluble in the orgnaic media (methylene chloride)

therefore, if no NaOH was added... choose organic layer (in the methylene chloride)