CycloEicosanone

I've mastered MOST aromatic substitution reactions, but I found one in my book that perplexes me. (Unfortunately the answer isn't at the back of the book.) In the reaction below, one might think that two products will form in a substituon reaction: an OH group in the ortho and para positions, relative to fluorine - since it is the least deactivating of the two substituents. However, something tells me that electrophillic substitution will occur since this is an acid-catalyzed reaction and it is carried out under warm condition. Therefore, the SO3H group will be replaced with a hydrogen, yielding simply, fluorobenzene. Can anyone enlighten me about which mechanism/product to expect? Thanks so much in advance! I really want to understand this so I can do well on next week's big exam, yet importantly become a good researcher someday!

As it turned out, there were several questions related to this matter on my o-chem test Monday and I got them all right...thank you once again

"When propene is treated with HCl in ethanol, one of the products of the reaction is ethyl isopropyl ether. Write a reasonable mechanism showing how this product forms. For each step of the mechanism, use curved arrows to show the direction that an electron pair moves when a bond is made or broken." Here's the reaction that I sketched out. It looks ok to me, but if someone could double check it for me I'd sincerely appreciate it! Just wanna make sure I got each subsequent transfer of electrons/breaking of bonds correct. Thanks!

Great, all I needed to know is that there will be cis AND trans isomers of my product...I know a lot about stereochemistry involving cis and trans isomers, enantiomers, etc but I'm just a bit unfamiliar with the products formed from a cyclic substrate. Thanks for clearing things up!

Hey guys, thanks for the help - it's much appreciated. However, I was just thinking and theoretically, could both cis and trans isomers be formed from the reaction? By that I mean the OCH3 group could be in the axial or the equatorial position. (Therefore, the trans form would be most stable since there'd be no 1,3-diaxial interactions?) Lemme know what ya think!

I am asked to predict product(s) of the SN1 reaction below and label the major (most stable) product if applicable. Should I be drawing more than one conformation of that product? Ex. a conformation that has the isobutyl group in the axial position, since there could be more than one 1,4-cis conformation? Any help sincerely appreciated, thanks!!

I know an enantiomer is simply a non-superimposable mirror image of a compound containing at least one stereogenic carbon, but for the life of me I can't figure this one out! Help would be sincerely appreciated, thanks!! (Please excuse my terrible drawings of the dashed lines.)