Destroyer orgo question

[dentistaa]

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Could you guys help me out with this queston plz?

#154. Which cpd is most acidic?
a)p-chlorophenol
b)p-nitrophenol
c)phenol
d)p-ethylphenol
e)p-methylphenol

the awnser is b), but I am not sure why b) is more acidic than a), both being EWG..

 

[ZH1988]

Could you guys help me out with this queston plz?

#154. Which cpd is most acidic?
a)p-chlorophenol
b)p-nitrophenol
c)phenol
d)p-ethylphenol
e)p-methylphenol

the awnser is b), but I am not sure why b) is more acidic than a), both being EWG..

nitro is a stronger electrophile than Cl

 

[dl9006]

can't there be resonance due to the NO2 group when you remove the proton from the OH?

the extra stabilization from the resonance structure lets it be more acidic, i think..

 

[ZH1988]

can't there be resonance due to the NO2 group when you remove the proton from the OH?

the extra stabilization from the resonance structure lets it be more acidic, i think..

yeah and thats exactly why nitro is more acidic cause all the Cl can do is donate electron to the ring which the O doesnt need..

 

[dl9006]

yeah and thats exactly why nitro is more acidic cause all the Cl can do is donate electron to the ring which the O doesnt need..

lol good to hear that i still remember something.

haven't studied much organic chem yet

and not looking forward to it...



how long did it take you guys to review all your organic?

 

[ZH1988]

lol good to hear that i still remember something.

haven't studied much organic chem yet

and not looking forward to it...



how long did it take you guys to review all your organic?

if u did good in ur class it should take 2-3 days
and if u can do destroyer you should be fine