I am trying to figure out if I am correct about the solubility of 9-fluorenone in NaOH and diethyl ether and the solubility of benzoic acid in NaOH and diethyl ether

9-fluorenone is soluble in diethyl ether because it can hydrogen bond with water so it is soluble in the diethyl ether?
And 9-fluorenone is insoluble in NaOH because 9-fluorenone is too big?

Benzoic acid is soluble in NaOH because it can hydrogen bond with NaOH?

2 answers

These are totally unreasonable answers.
Thanks for the answer, chem geeks!