Question

Hello guys! Just reviewing my Chemistry study guide, we did a lab where we nitrated Napthalene. Something to know, the mononitration of Napthalene gives me 1 of 2 possible products: 1-nitronaphthalene or 2-nitronaphthalene.

Please predict the reaction by drawing ALL resonance structures for the carbocation intermediate (arenium ion) for both 1-nitronaphthalene and

2-nitronaphthalene and predict the major product based off the most stable carbocation intermediate.

Here is the overall reaction if needed:

ΝΟ, NO HNO H,SO 1-nitronaphthalene m.p. 61°C 2-nitronaphthalene m.p. 79°C

Answer 1

Nitration of Napthalene. HNO3 H, Sou Hoog + H₂SO4 H₂ No No t HO 1-nitronaphthalene mechanson wou Have Ney NO₂ NOL 2- nitronaph thalene mechanism mesiate formes As, we can see the carbocation intermediate ho & when hitration occups at C-1 has greater number of resonance contributing structure that (-2, thus the major product will be. 1-nitronaphthalenel structure thanfon