MechRocket Posted February 28, 2010 Share Posted February 28, 2010 Hello all, I have a midterm on Monday and was hoping I could get a question answered. 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! Link to comment Share on other sites More sharing options...
Horza2002 Posted February 28, 2010 Share Posted February 28, 2010 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. Link to comment Share on other sites More sharing options...
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