What order would these compounds elute in a 3:1 hexanes:ethyl acetate TLC run?
Making predictions about elution order is always guesswork but based on my experience I would expect acetic acid to streak off the baseline, The benzyl alcohol to be of low Rf but above the acetic acid, the benzyl acetate Y to run high and I really don't know about the acetic anhydride, I suspect it will hydrolyse on the plate to give you more acetic acid so you will not see a separate spot. How are you planning on visualising these?