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Why doesn't the benzene get protonated in this problem?

MechRocket
in Organic Chemistry

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Hello all, I have a midterm on Monday and was hoping I could get a question answered.

 

wtfot.jpg

 

Why doesn't the benzene grab that proton from the H2SO4? My answer key has the molecule on the right grabbing the proton instead.

 

My logic: if the benzene grabbed the proton, a secondary allylic carbocation would be formed with a lot of conjugation in the molecule. I would expect this to be more stable than the tertiary carbocation that is formed if the molecule on the right gets protonated.

 

So why does the benzene not get protonated?

 

Thanks!

Benzene is an extremely stable molecule because it posses aromatic stabilisation. Sulphuric acid is not strong enough to distrupt this stabilising energy of benzene by protonating it.

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