Nucleophile vs Electrophile

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Ajith Raja 2L
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Joined: Wed Nov 18, 2015 3:00 am

Nucleophile vs Electrophile

Postby Ajith Raja 2L » Fri Mar 10, 2017 1:17 pm

I had a question on identifying if something was an electrophile or a nucleophile. Doesn't it depend on what the molecule is surrounded by rather than the molecule itself? Because couldn't a molecule be a nucleophile but if it is surrounded by different molecules it could be an electrophile? Thank you.

Christine_Mavilian_3E
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Joined: Fri Jul 22, 2016 3:00 am

Re: Nucleophile vs Electrophile

Postby Christine_Mavilian_3E » Fri Mar 10, 2017 1:31 pm

Generally speaking, you can identify whether something is a nucleophile or electrophile simply when the molecule is by itself. For instance, Cl- is a nucleophile while neutral Cl is an electrophile. However, if you combine molecules to form a compound, the compound can be a nucleophile or electrophile regardless of what the molecule is by itself. For instance, Cl- is a nucleophile but AlCl3 is an electrophile.

I hope this answers your question!

DanielaWong_2G
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Joined: Wed Sep 21, 2016 2:56 pm

Re: Nucleophile vs Electrophile

Postby DanielaWong_2G » Fri Mar 10, 2017 2:13 pm

I think it has to do with whether or not the molecule has electrons that are readily available. If it does, it would be considered a nucleophile

Michael Lesgart 1H
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Re: Nucleophile vs Electrophile

Postby Michael Lesgart 1H » Sat Mar 11, 2017 3:32 pm

Also, it is useful to note electronegativity in a molecule that can cause it to become an electrophile. For example, CO2 is an electrophile because of the dipole moments created by the negative charge of the O with the positive charge of the C, and the electronegativity of the Oxygens cause the Carbon to become more positive in charge, thus making CO2 an electrophile.

Amber Duong 1B
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Re: Nucleophile vs Electrophile

Postby Amber Duong 1B » Sat Mar 11, 2017 5:39 pm

Generally, a nucleophile is a molecule that has lone pairs to donate and can be neutral or negatively charged (more electronegative). On the other hand, electrophiles want to have a complete set of 8 valence electrons and are usually neutral or positively charged (less electronegative). The surroundings of a molecule dictate whether the electrons favor one molecule over another due to differences in electronegativity.

Samuel_Vydro_1I
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Re: Nucleophile vs Electrophile

Postby Samuel_Vydro_1I » Sun Mar 12, 2017 6:47 pm

Nucleophile is simply a fancy way of saying -- molecule that has a lone pair to bond with a molecule that needs an electron. Electrophile is a fancy way of saying-- molecule that needs an electron. Cl to Cl- is something you can remember from 14a


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