electrophilicity comparison

[yui_96]

Why is acetone a better electrophile than tertbutanol?

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[mtn_dew0verdose]

Acetone has a double bonded oxygen which pulls electron density towards the oxygen and away from the carbon, giving the carbon a partial positive charge, thus giving the carbon an electrophillic property

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[aldol16]

Ketones and aldehydes will always have more electrophilic carbons (the one participating in the double-bond) than alcohols.

 

[yui_96]

Acetone has a double bonded oxygen which pulls electron density towards the oxygen and away from the carbon, giving the carbon a partial positive charge, thus giving the carbon an electrophillic property



Why would a double bond matter?

 

[JustinM88]

Acetone has a double bonded oxygen which pulls electron density towards the oxygen and away from the carbon, giving the carbon a partial positive charge, thus giving the carbon an electrophillic property

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I would also like to add that, for the tertbutanol, due to the Inductive Effect, the 3 alkyl groups (the methyl groups here) are electron DONATING, so that C in the middle there has even more electron density than normal, which obviously makes it less positive and thus a worse electrophile

 

[mtn_dew0verdose]

Double bonds hog up electron density

 

[yui_96]

I would also like to add that, for the tertbutanol, due to the Inductive Effect, the 3 alkyl groups (the methyl groups here) are electron DONATING, so that C in the middle there has even more electron density than normal, which obviously makes it less positive and thus a worse electrophile

You should be my MCAT tutor

 

[JustinM88]

You should be my MCAT tutor

haha I am flattered, and I actually was recruited to be a tutor at my local community college for Gen Chemistry I/II + Organic Chemistry I/II ^.^
I will say though that I'm probably average in terms of my MCAT scores as of now for General Chemistry (still have 2.8 months to go though hehe).