OC achiever - help!

[ddstobe]

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phenol < ethanol < isopropyl-OH < tert-OH

ascending basicity

WHY???😕😕😕

this is suppose to be a simple question and obviously I'm not ready for tomorrow's DAT!!!🙁

 

[ddstobe]

please somebody...

 

[ddstobe]

someone's dying over here! SOS!!!

 

[ddstobe]

ok, I officially believe no one knows the "why."

 

[Ruthless]

basicity increases if there r more e-donating groups like alkyl groups

 

[211183]

ok, I officially believe no one knows the "why."

lol ddstobe talkin to himself...
gah i know how you feel though man test tomorrow and you're like wait what!!
mine is tomorrow too and i'm doing the same thing as you... prac probs... then freaking out

all i can say is phenol is more acidic... so its less basic... its more acidic because of the electron withdrawing effect of the ring...

not sure about the others... 🙁 it's depressing me, too.


maybe the greater the alkanes are more and more e-donating, make it more basic?

 

[ddstobe]

lol ddstobe talkin to himself...
gah i know how you feel though man test tomorrow and you're like wait what!!
mine is tomorrow too and i'm doing the same thing as you... prac probs... then freaking out

all i can say is phenol is more acidic... so its less basic... its more acidic because of the electron withdrawing effect of the ring...

not sure about the others... 🙁 it's depressing me, too.


maybe the greater the alkanes are more and more e-donating, make it more basic?

wait...I thought -OH is e- activiting group (= donating group right?!!)

 

[211183]

wait...I thought -OH is e- activiting group (= donating group right?!!)

i think the ring is E- W tho... its a "sub" on the -oH... rem reading it. just tryin ot help i think my brain said... im going to sleep bc i dont want to take your stupid DAT exam

 

[anesthesia_209]

wait...I thought -OH is e- activiting group (= donating group right?!!)

It is, which is one of the reasons why the phenol is the most acidic. O is donating so it can donate electrons into the ring after being deprotonated, making it more stable. (resonance increases acidity and stability). The aromatic ring is a withdrawing group.

Alkyl groups are donating groups, but they are connected to O, which is bad. The O is trying to spread out the charge but the carbons aren't helping by donating, which results in it being less stable and there fore less likely to get rid of the hydrogen. The more alkyl groups you have attached, the more basic it is. The more electronegative/withdrawing groups you have attached, the more acidic.

 

[tranv117]

more Cs more electron donating. So you can see why t-OH is the greatest base and descends with the others that have less Cs. Electron donating makes O have more electron density and greatest capability of picking up an extra proton making it more basic.

Now with phenol, you are right that OH substituent is an electron donating group to the ring. Hence less electron densed at O so less capable/willing to pick up the H so its the weakest base.

 

[ddstobe]

thank you guys, i feel a lot better now.

 

[211183]

Oooooo