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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Woopy on April 08, 2013, 09:07:53 PM

Title: Protonating oxygen on a carbonyl
Post by: Woopy on April 08, 2013, 09:07:53 PM
Hello,

I was wondering, why does protonating the oxygen on a carbonyl compound increase the electrophilicity of the carbonyl carbon? Wouldn't it be pushing electron density toward the carbon, since the oxygen is not pulling the density away as much since it is positively charged?
Title: Re: Protonating oxygen on a carbonyl
Post by: discodermolide on April 08, 2013, 09:28:06 PM
Well I think that oxygen does not really like to carry a positive charge. So putting one on a carbonyl oxygen by protonation will cause the electrons to drift towards the oxygen to try and compensate for the charge, this results in the carbon atom becoming more positive, i.e. a better electrophile.
Very simplistic explanation. Perhaps someone can be more scientific?
Title: Re: Protonating oxygen on a carbonyl
Post by: Dan on April 09, 2013, 03:26:04 AM
Wouldn't it be pushing electron density toward the carbon, since the oxygen is not pulling the density away as much since it is positively charged?

I don't understand your logic. If something is positively charged, what does it attract?