Ortho Para Ratio - Aromatic Nitration of Toluene

This organic chemistry video tutorial provides a basic introduction into the ortho para ratio of the aromatic nitration of toluene. Bulky groups such as the tert-butyl group favor the para product while the small substituents such as the methyl group favor the ortho product.
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[@Jane-jx7nr]

While my chemistry classes might have my professors' names listed, make no mistake, you are the one who is actually teaching me.

[@francesanne6135]

Why isn’t NO2 meta-directing?

[@notinterested4263]

Bro NO2 is Mete directing but -Ch3 group is op directing.

[@f_norfazrihanakmamustafa5072]

why did unbulky substituent favor ortho?

[@PunmasterSTP]

I think it's because there are two ortho positions compared to one para. So if there were no steric effects, we'd expect there to be 66% ortho and 33% para (leaving off repeating decimals). With steric effects, it pushes that ratio lower, but there might still be more than 50% ortho.

[@safeenagul2768]

Sir plz tell me how we calculate artho para ratio

[@PunmasterSTP]

I don't think it's something you can calculate; rather, you (or someone else) has to run the reaction and measure the ratio. I think you can use reasoning about steric hindrance and other phenomena to try to find supporting reasons, but I don't think there is an actual formula that you can use.

[@vincentrotichrotich6653]

I learnt alot.......burr if only you could show how to calculate the O/P ratio.....

[@PunmasterSTP]

I don't think it's something you can calculate, at least not accurately with a simple formula. But you can reason that if there were *no* steric effects, then you should have 66% ortho and 33% para (leaving off the repeating decimals), since there are two ortho positions and one para (2:1 ratio or 66% to 33%). When there is steric hindrance, it favors the para position more. But since there are two ortho positions compared to one para, you might still have more than 50-50 ratio (like 60% ortho and 40% para or something like that).

[@sakhemcetywa6847]

thanks organic chemistry tutor✌

[@benwilliams1889]

4:40.. If the alkyl groups provide electron releasing inductive effect stabilizing the compound at the ortho site, wouldn't this cancel out the bulkiness of the tertbutyl group? Also, there are two ortho attachments but only one para, wouldn't this increase the ortho ratio?

[@csirnetandsyntheticchemist2681]

How we calculate the % of ortho Para ratio

[@PunmasterSTP]

I don't think you can. I think this is something you would just have to measure (or look up somewhere).

[@yashyadav5987]

I have a doubt that when any electrophile attacks on toulene it attacks where charge density is more and when we attack any electrophile on 2 methyl butane. and if the negative charge is on 2nd position it is unstable and the more we do hydride shift towards 3rd and 4th position the more it becomes likely to be attacked by any electrophile but why
.....charge density was more on 2nd as compared to 3 rd and 4th but in toulene we attacked the electrophile where charge density was maximum

[@safeenagul2768]

Percentage ***

[@intan3415]

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[@Tolumak.]

Isn't no2 meta directing

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[@vijaychaturvedi5928]

How ter butyl show resonance