Which carbon in a double bond does the electrophile bond to

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cmmurphy_4G
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Which carbon in a double bond does the electrophile bond to

Postby cmmurphy_4G » Thu Mar 03, 2016 8:53 am

When a double bond acts as a nucleophile and donates electrons to an electrophir, how do you know which carbon the electrophile is going to bond to? On page 152 in the organic chem textbook, the hydrogen bonds to the last carbon, but could it have bonded to the second carbon as well?

VictoriaRoderick_3A
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Re: Which carbon in a double bond does the electrophile bond

Postby VictoriaRoderick_3A » Thu Mar 03, 2016 9:28 am

As long the molecule is symmetrical, you can attach it to the either carbon. The halogen then attaches to the carbocation.

cmmurphy_4G
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Joined: Fri Sep 25, 2015 3:00 am

Re: Which carbon in a double bond does the electrophile bond

Postby cmmurphy_4G » Thu Mar 03, 2016 1:43 pm

What if it's not symmetrical?

Chem_Mod
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Re: Which carbon in a double bond does the electrophile bond

Postby Chem_Mod » Thu Mar 03, 2016 5:36 pm

Markovnikov's Rule states that the hydrogen will attach to the carbon which already has more hydrogens on it.

An equivalent statement is that the halogen (eg. Br) will attach to the carbon that was more highly substituted (the carbon with less hydrogens)


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