Electrophiles are one of the two most important reactants in organic chemistry.  As we have discussed previously on this blog, organic chemistry reactions are all about the flow of electrons, and electrophiles are the ones who want those electrons. When you think of the word “electrophile” you should think of the Greek word “Philos” which means “to love”.  Therefore, an electrophilic species is one that loves electrons.  Easy enough, right?   Since opposites attract, and the electrophile loves electrons, then it must be that the electrophile is positively charged. Most often, you will see this abbreviated as “E+”.

So the question now becomes: what make an atom a good electrophile and how do we spot it? Since we know the electrophiles want to electrons, the first clue that something is electrophilic is that it has a positive charge. The second clue is if we can place a positive charge somewhere on the atom via resonance and that it has an empty orbital (positive charge or metal with an empty orbital) or can get an empty orbital by kicking off a leaving group.  Below are some common classes of electrophiles you will see frequently in your course:

In example A, a carbonyl is shown. We know that the carbon of the carbonyl is electrophilic because we can place a positive charge on it via resonance. This means that a nucleophile will attack the carbonyl at this carbon atom.  In example B, we show diatomic chlorine. Diatomic halogen molecules are electrophilic because the bond between the halogen atoms as polarizable, meaning that the electrons can reside on either atom at any time, making one of the atoms more electrophilic than the other.  In example C, we see that alkyl halides are also electrophilic because of a polarizable bond between the carbon and the chlorine atoms.  Unlike example B, example C is a permanent dipole.  Example D is an example of a strong acid completely disassociating, which gives off a proton as the electrophilic species. Finally in example E, we see it you can create an electrophile from a non-electrophilic molecule. Here we have reacted nitric acid with sulfuric acid to form the nitronium ion, which is highly electrophilic.

Take home points on electrophiles:

1)      They want electrons, meaning they are electron deficient.

2)      They are attacked by nucleophiles.

3)      They are positively charged, polar and/or polarizable.

4)      They become better electrophiles in the presence of Lewis acids.

Would you like to learn about the nucleophiles that will attack these electrophiles?  Please go to strong nucleophiles to get a good flavor of those.

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As the fall semester grows closer, I will remind everyone of this again, but here is something to think about now.  If you are taking freshman chem now or know you are going to take sophomore organic chemistry next year, find out which book your university uses.  Usually, there is one textbook that all the profs at one school use.  Once you know which book it is, go online and buy a copy before the class starts.  What unfortunately happens to alot of students is that they don’t know what text is used til the class starts.  Then it is too late to buy it online because the shipping takes too long (unless you pay the big bucks).  I was shocked what a big difference in price there is between used organic chemistry books and new ones (prices listed below are from Amazon).

Organic Chemistry by Solomons; $194 New, $32 Used

Organic Chemistry by Carey; $162 New, $79 Used

Organic Chemistry by McMurry; $192 New, $164 Used

Think about all of the wonderful things you could buy with the extra bucks: Admission to a StarWars convention, extra value meals for all of your friends at McDonalds, the extra fancy car wash, a couple of months of your favorite pay-per-view channels.  The possibilities are endless.

Anywho, just something to think about.  Good luck with the semester and as always, happy reacting.

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Good luck with those classes coming up and as always, happy reacting.

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Thanks for reading, for more organic chemistry help, please go to AceOrganicChem.com, and as always, happy reacting.