28
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Friedel–Crafts reaction of phenol
Like aniline, phenol too reacts to a very less extent during Friedel-Crafts reaction.
The reason being that the oxygen atom of phenol has lone pair of electrons which coordinate with Lewis acid.
...
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18
votes
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Acidity of substituted phenols
I would appreciate learning whether such reasoning, for these two
type of substituted phenols is plausible or whether furthermore
solid arguments should be invoked.
Your reasoning seems generally ...
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18
votes
Benzene to phenol in a single step
The reaction of benzene over $\ce{V2O5/ PtAu}$ catalyst at lower temperatures, can convert benzene to phenol with some success.
See this book here Direct hydroxylation of benzene
[The original ...
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16
votes
Acidity order of nitrophenols
You have correctly identified that m-nitrophenol should be the weakest acid among the isomers as the resulting anion cannot be stabilised by the $\text{-M}$ effect of nitro group owing to its meta ...
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14
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Friedel–Crafts reaction of phenol
To add to @user223679's answer. Phenol can react via two pathways with acyl chlorides to give either esters, via O-acylation, or hydroxyarylketones, via C-acylation.
However, phenol esters also ...
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14
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Why is meta-nitrophenol less acidic than para-nitrophenol?
The acidity of nitrophenols (or any acid for that matter) is determined by the stability of the conjugate base. In the case of m-nitrophenol and p-nitrophenol, the relative stability can be determined ...
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13
votes
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Aromatic ether to phenol reagents
The reaction is demethylation of methoxybenzene. You can do it by using an acid which has a nucleophilic counter ion.
It is not actually obvious why the iodine nucleophile attacks the methyl group ...
- 607
12
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Why isn't 4-hydroxybenzoic acid formed along with salicylic acid in Kolbe's reaction?
I don't understand why two different products are formed in the same reaction using very similar bases.
If the bases make a a difference, there must be a difference between them.
If the anion is the ...
11
votes
Can phenol be detected with a ceric ammonium nitrate test?
With unsubstituted phenol ($\ce{PhOH}$) dark-brown precipitation is formed:
$$\ce{(NH4)2[Ce(NO3)6] + 2 PhOH -> [Ce(NO3)4(PhOH)2] + 2 NH4NO3}$$
Other phenols should produce wine-red solution as ...
- 34.7k
11
votes
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Reimer–Tiemann-like reaction of catechol with diiodomethane
This is not really an answer to your question, but I do not think that it is possible to answer it. From one of the many comments we learn that the reference is actually the "preparation of ...
- 42.2k
10
votes
Synthesis of 2-methyl-4-nitrophenol from benzene?
There is a lot of good thinking in your proposed synthetic strategy. The one major shortcoming is, as @Mithoron points out, $\ce{OH^{-}}$ is not an electrophile.
We need to introduce a methyl, ...
- 81.6k
10
votes
Can the hydroxyl group of 4-hydroxybenzoic acid react with phosphorus pentachloride?
a phenol will not react (or react very slowly) with $\ce{PCl5}$
That's not true. Phenol and $\ce{PCl5}$ do react, producing mixture of compounds of formula $\ce{PCl_n(C6H5O)_{5-n}}$ (with $n > 1$ )...
- 20.6k
10
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Strength of hydrogen bonding in phenol or methanol
Let me answer the second question first, because the answer is so much easier: Of course the hydrogen bond strength depends among others upon the carbon oxygen is attached to. Consider phenol and ...
- 63.7k
10
votes
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What is the product of the chemical reaction between phenol and ferric chloride?
After doing some looking around, and going back to check what I thought I knew about coordination complexes, I think I understand why you're seeing two equations. I first recommend reading the pages ...
- 166
10
votes
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Phenol smell from hands
As an acidic compound, phenol started to degrade the protective layers of your skin, and partially diffused into deeper layers. This, and because of the moderate solubility in water are the reason ...
- 23.6k
10
votes
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Reaction of phenol and zinc dust
Ludwig Gattermann's The Practical Methods of Organic Chemistry (translated into English, 1896) has two references to reduction of aromatics with zinc dust:
The first one refers to Liebigs Annalen, ...
- 30.1k
10
votes
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Reaction mechanism of rearrangement
The first reaction is O-alkylation of p-cresol to give a 4-methylphenyl allyl ether derivative 3. The reagent in the first box should be 1-bromo-3-methylbut-2-ene (1; see the top box in the picture), ...
- 34.7k
9
votes
How are phenols made?
That reaction will definitely not yield a phenol.
Phenols are not usually prepared directly from benzene, but from benzene derivatives, such as toluene or chlorobenzene:
Oxidation of toluene, as ...
- 1,964
9
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Electrophilic Aromatic Substitution: Are protonated OH-groups ortho-/para- or meta-directing?
O-protonated phenols direct in meta, according to an article on that topic. As it occurs, phenols can be, depending on acid, protonated on oxygen, but also on carbon. They can even be diprotonated, ...
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votes
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Why is picric acid more acidic than carbonic acid?
So you want to compare the acidity of different Brønsted–Lowry acids. This means ultimately you want to compare the equilibrium constants for reactions of the type $\ce{HX <=> H+ + X-}$. To do ...
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9
votes
Halogenation of Phenol
The reaction of phenol with bromine is known as bromination of phenol. Solvent has great influence on the reaction. In different solvents, different products are obtained. The action of bromine on ...
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8
votes
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Why is a hydroxyl group more activating than a methoxy group in electrophilic aromatic substitution?
First of all we must have to note that the difference in reactivity between anisole (methoxybenzene) and phenol is small. Small enough for the undergraduate texts I own to not mention anisole ...
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8
votes
Aromatic ether to phenol reagents
Boron tribromide is a standard reagent for cleaving aryl methyl ethers to the corresponding phenol. It is a general method and can be used in aromatic methyl ethers with sensitive substituents where ...
- 81.6k
8
votes
Why is the para product major in the nitrosation of phenol?
Ortho and para positions are activated due to the +R effect of the $\ce{-OH}$ but the preference of the para product can be explained by the mechanism.
The mechanism proceeds through a dienone....
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8
votes
Gattermann-Koch Reaction with Phenol Substrates
You have outlined that the formyl chloride is generated as the reactive, electrophilic intermediate under these conditions.
You are planning to perform an electrophilic aromatic substitution, but in ...
8
votes
Between 3-chlorophenol and 3-fluorophenol, which one is more acidic?
Experimentally, the $\mathrm pK_\mathrm a$ values for 3-chlorophenol and 3-fluorophenol appear to be (perhaps unexpectedly) equivalent.
The table below1 shows the measured $\mathrm p K_\mathrm a$ ...
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7
votes
Selective alkylation of carboxylic acid versus phenol
Using the haloform reaction to convert the methyl ketone 1 to the corresponding carboxylic acid 2 is a neat idea. According to an old review by R. C. Fuson and B. A. Bull, published in Chem. Rev., ...
7
votes
Inductive vs resonance effects and the acidity of phenol
That blog post you are referencing voices very strong opinions with which one can agree or disagree. I personally love one of the comments under the blog saying
I judge people by the units they use....
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7
votes
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Suggestion for a Synthesis of Paracetamol — plausible?
Your route sounds possible, yes. (Aniline is commercially available.) There would very likely be side reactions of the amide under Baeyer-Villiger conditions but nothing exceptionally out of control—...
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