Which would have a lower Rf value? 1,2-cyclohexanediol or benzoic acid? I am confused because benzoic acid has an aromatic and carboxylic acid; and 1,2-cyclohexanediol has an aromatic and 2 alcohols.

Question

anonymous · Answer

According to a chart I have, carboxylic acids are more polar than alcohols, but I get confised thinking that there are two alcohols.

aaronq · Answer

is the benzoic acid is protonated (i.e. not a salt)?

anonymous · Answer

yes?

aaronq · Answer

if it wasn't protonated i would say definitely yes. But, even if it is, i would think it had a lower retention factor (in a normal phase TLC plate).

anonymous · Answer

How would I know if its protonated? I was given a question for a prelab to arrange in order of increasing Rf ( I assumed that we had to do it using the formal group's present in the compund). So far, I managed to identify all of them, except the 1,2-cyclohexanediol and benzoic acid.

aaronq · Answer

They would have to tell you. I would put that benzoic acid is more polar than 1,2 cyclohexanediol

anonymous · Answer

ok, would it be because it has two alcohols?

aaronq · Answer

because you're comparing 2 hydroxyls to 1 hydroxyl + 1 carbonyl

anonymous · Answer

nevermind, I understood what you said. sorry

anonymous · Answer

thank you!

aaronq · Answer

no problem !