Aromatic question

This forum made possible through the generous support of SDN members, donors, and sponsors. Thank you.

kingseven

Full Member
7+ Year Member
Joined
Dec 19, 2013
Messages
82
Reaction score
6
Hey guys, I was doing Chad's aromatic quiz and I don't understand why I got this question wrong. Can anyone please explain this to me. Thanks
 

Attachments

  • Aromatic.png
    Aromatic.png
    42.3 KB · Views: 91
Well the oxygen has 2 lone pairs and one of them contributes to the structure giving it 6 pi electrons thereby following Huckels rule and the plus charge on the carbon indicates that it is sp2. So since it is cyclic, planar, sp2 and obeys huckels rule you can determine that it is aromatic.
 
Since the lone pairs (pi electrons) on the oxygen are not associated with a double bond, they are able to participate in resonance. Therefore the 4 delocalized electrons in the ring and 2 from the oxygen make a total of 6 delocalized electrons able to perform resonance. With the help of the "+" charge on the allylic carbon, the molecule is an aromatic compound
 
I was first thinking about the lone pairs on the oxygen and then i was like since its not mentioned I should look at it without the lone pairs. But I guess on the real DAT you have to be careful even if the lone pairs are not mentioned. Thanks guys
 
Top