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 ...
- 39.1k
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 ...
- 5,375
14
votes
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 ...
- 15.3k
12
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 ...
- 37.4k
12
votes
Accepted
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 ...
- 43.8k
11
votes
Accepted
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 ...
- 28.4k
11
votes
Accepted
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), ...
- 39.5k
10
votes
Accepted
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 ...
- 176
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, ...
- 84.2k
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, ...
- 39.2k
9
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....
- 5,504
9
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 $\mathrm p K_\mathrm a$ ...
- 17.1k
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 ...
- 330
8
votes
Accepted
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—...
- 67.3k
8
votes
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Reactivity comparison of phenol and toluene towards electrophilic substitution
You have to make a comparison between phenol and toluene. You have identified what toluene does, but you haven't described what phenol does.
The hydroxyl group in phenol increases electron density in ...
- 9,688
8
votes
Accepted
Partial oxidation of toluene
You can justify the formation of Benzaldehyde from Toluene by oxidising with peroxide just by looking at the mechanism of the reaction and think of migratory aptitude of Phenyl group , hydride and ...
- 5,593
8
votes
Reaction mechanism of rearrangement
Potassium carbonate is a perfectly good base for the alkylation of phenol ($\mathrm{p}K_\mathrm{a} = 10$) with a good electrophile, in this case 3,3-dimethylallylbromide. The reaction you are looking ...
- 21.6k
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....
- 67.3k
7
votes
Can phenol be detected with a ceric ammonium nitrate test?
I have mentioned CAN test of alcohol and phenol in a previous answer of mine, so I am going to directly quote that:
Genereally, CAN test is done for alcohols which give pink or red
colour. But ...
- 25.2k
7
votes
Out of the given reagents, find the ones to be used to convert benzene to p-aminophenol
Steps:
Use $\ce{Br2/FeBr3}$ to make bromobenzene.
Nitrate with $\ce{HNO3/H2SO4}$ to make 4-bromo-nitrobenzene.
Treat with $\ce{NaOH}$ to displace the $\ce{Br}$ making 4-nitrophenol.
Reduce with $\ce{...
- 21.6k
7
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Why does the -OH group in β-naphthol direct the incoming diazonium salt towards the ortho position?
It's sort of a process of elimination. The electrophilic ion could potentially attack anywhere, but:
The hydroxyl group is activating, so the electrophile will prefer that ring. You are left with ...
- 53.4k
6
votes
Why is a hydroxyl group more activating than a methoxy group in electrophilic aromatic substitution?
Mechanism of electrophilic aromatic substitution to both phenol as well as anisole involves attack of the electrophile to the electron rich $\pi$ nucleus of the aromatic system.
In anisole the ...
6
votes
Reimer–Tiemann-like reaction of catechol with diiodomethane
Catechol does react with diiodomathane in presence of $\ce{NaOH}$ as the base. But it does not perform Reimer-Tiemann reaction, but instead it forms methylenedioxybenzene (2H-1,3-Benzodioxole is the ...
- 5,647
6
votes
Accepted
Phenol preparation from Grignard reagent
As requested by the OP - the route that lab chemists use to form phenols from aryl halides (not aryl fluorides) is via formation of the aryl boronic acid or boronate. These may be formed by either ...
- 21.6k
6
votes
Accepted
pKa of phenols using UV-Vis spectroscopy
To quote the key points of an easy to read publication by Salgado and Vargas-Hernández (doi 10.4236/ajac.2014.517135, open access):
All starts with the dissociation equilibrium between the acid $\ce{...
- 28.4k
6
votes
Does boric acid really rearrange phenols?
Prepchem.com apparently misinterpreted what was in the patent.
The abstract of the patent reads:
A process for preparing hydroxyphenyl ethers by oxidizing phenyl ethers with hydrogen peroxide in the ...
- 53.4k
5
votes
Which Phenols give the colours blue, green or violet in the neutral FeCl3 test?
The color of the solution will depend on what substituent is attached to phenol. The following is an excerpt from an e-book:
Ferric Chloride Test: To 2 ml aqueous or alcoholic solution of compound, ...
- 25.2k
5
votes
How does the solvent determine whether mono- or tribromination of phenol occurs?
In aqueous medium, phenol is deprotonated to a certain extent, forming the phenoxide ion in which the ortho and para positions are even more activated than in phenol itself. Hence, trisubstitution ...
- 651
5
votes
Accepted
What is the reason for the acidic character in phenols?
You are confusing the two terms electronegativity/electropositivity and higher/lower electron density.
The source you read states that the $\ce{sp^2}$ hybridised carbon in phenol is more ...
- 67.3k
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