question about ochem for achiever #2

[omegax8]

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on # 71 of the achiever test # 2 for ochem, the question asked me to list the compound based upon increasing basicity. the answer choice is D stating the phenol is the weakest followed by ethanol then isopropyl and then tbutyl(as the strongest base). I was a little confuse about this since i thought the the strongest base would be the weakest acid and since phenol is the strongest acid i could understand why it is the weakest base. but then the other choices kinda change after that because it would seem that t butyl is the next strongest acid followed by isopropyl and then ethanol. so shouldn't so how the answer be phenol<tbutyl<isopropyl<ethanol in basicity??

 

[dlink]

on # 71 of the achiever test # 2 for ochem, the question asked me to list the compound based upon increasing basicity. the answer choice is D stating the phenol is the weakest followed by ethanol then isopropyl and then tbutyl(as the strongest base). I was a little confuse about this since i thought the the strongest base would be the weakest acid and since phenol is the strongest acid i could understand why it is the weakest base. but then the other choices kinda change after that because it would seem that t butyl is the next strongest acid followed by isopropyl and then ethanol. so shouldn't so how the answer be phenol<tbutyl<isopropyl<ethanol in basicity??

t-butyl alcohol is most basic here because t-butyl is a stabilized tertiary carbocation when the alcohol picks up a H+ from the surrounding to lose its OH- {Bronsted rule here I believe}.