Once phenol is nitrated, would the major organic product formed be: ortho, meta, para or a combination?
I'm assuming you mean if phenol is nitrated, not after it's nitrated. In that case, phenol is otherwise known as hydroxybenzene.
The hydroxyl group is an electron-donating group. Those strongly-activate the ring for electrophilic aromatic substitution, the mechanism of nitration, at the ortho + para positions.
The following is the nitration mechanism for just benzene.
- Nitric acid has a higher pKa than sulfuric acid (
#-1.3# vs.#-3# ), so it is readily protonated. NOTE: In order for the mechanism to proceed, it must be protonated on the hydroxyl!- The newly-generated
#"H"_2"O"# leaving group leaves, giving an activated nitronium ion.- This becomes the electrophile for the nucleophile to attack in electrophilic aromatic substitution (EAS).
- The EAS mechanism finishes when some base comes in to eliminate the proton adjacent to the carbocation, restoring aromaticity.
Maybe you can analogize with phenol; the only difference is that an
#"OH"# is on the top-middle carbon.Strongly-activating groups are ortho/para directors, but the nitration product would be a mixture (not combination) of the ortho and para products.
- The newly-generated
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The major organic product formed when phenol is nitrated is meta-nitrophenol.
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When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.
When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.
When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.
When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.
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