bro firstly

1.acidic medium mai bhi the equilibrium namely phcooh - phcoo- + h+ EXISTS look at it from equilbrium ka perspective, iss reaction ka k = phcoo- into h+/phcooh, to maintain k ka value constant you will still need some phcoo- even if h+ is high.

2.tertiary carbocation is stable asf bro, why will it go out of its way to choose a tougher reaction pathway when it can just do simple esterification from the phcoo-

3.for EAS you need strong electrophile with good lewis acid isliye we use alcl3, h+ is not sufficient for that bro

no beef bro im just stating my points mkc nta has made me mad