using reversed plate TLC and aqueous methanol as the mobile phase, which range from lowest to highest Rf value

Question

Benzoic Acid, Napthalene, phthalic acid and phenol?
And how do you figure out that which ones are lower and which are higher??
THANkkSS!!

Answer 1

I am going to guess benzoic acid will be most polar hence it will travel farthest on reverse phase. Phthalic acid has two acid functions but will be less polar due to intramolecular hydrogen bonding. Phenol may travel more or less than phthalic acid but napthalene will certainly travel least of all ( only hydrocarbon in group). In order to tell the compounds apart in a mixture you could separate the four compounds and take an IR of each compound. The two acid compounds will differ due to intramolecular hydrogen bonding/ Phenol will not have a carbonyl band at 1715 cm-1 but will have an -OH at 3100 cm-1 and naphthalene will have neither band.

Answer 2

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