Orgochem question-----help

[x-linked]

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1. is the nitrogen in pyrrole sp3 hybridized or sp2? from mcmurry's chem book, it says sp2 but from kaplan it says sp3. i am confused

 

[wammmy]

After taking the live kaplan classes I found all kinds of errors in the thier book, so if I had to guess I would say go witht the other source. However I don't know nor do I have a text with me to confirm.

 

[sinned]

since the nitrogen has three bonds and a lone pair, it is sp3 since a lone pair counts toward it's coordination number...

 

[bpenly]

It is SP2. Pyrrole is planar and the lone pair is in an unhybridized orbital (preventing sp3 and making it a poor base) and is part of the aromatic sextet.

This is straight from my textbook, Organic Chemistry by Brown and Foote, 3rd edition (2002).

 

[sinned]

oh yea, when compounds are aromatic, you can throw everything you learned out the gutter 🙂 yea it is planar and is most likely sp2 like bpenly said...

 

[x-linked]

thank you !