Antiaromatic Compounds

[ANEShopeful2018]

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Hey guys!

This question was in the Kaplan Review Notes for Orgo...basically it gave 3-bromocyclopentene and 5-bromocyclopent-1,3-diene. They say that once the bromine atom is taken off, the pentene is more stable than the diene because is diene is antiaromatic...but, it still has one more resonance structure than the pentene. So should it be more stable?

 

[ANEShopeful2018]

Ohh ok thanks! That makes sense. Here's another question for ya (I didn't feel like making another thread haha). Basically, there are 2 molecules: 1,1,1-trichloro-2-pentanone and 1-amino-2-pentanone, and it asked for the more acidic hydrogen. My thoughts are that the amino group provides an extra resonance structure that the trichloro ketone does not...in addition, the 3 chloro groups, while electronegative, are 3 bonds away. I have been told that resonance > inductive effects, and that inductive effects drastically decrease with distance. Right or wrong?

Thanks again!