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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 ...
AChem's user avatar
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15 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 ...
Archer's user avatar
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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 ...
bon's user avatar
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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 ...
andselisk's user avatar
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12 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 ...
Martin - マーチン's user avatar
11 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 ...
Buttonwood's user avatar
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11 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, ...
Karsten's user avatar
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11 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), ...
Mathew Mahindaratne's user avatar
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 $\mathrm p K_\mathrm a$ ...
NotEvans.'s user avatar
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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....
Avyansh Katiyar's user avatar
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 ...
Uday's user avatar
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8 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—...
Jan's user avatar
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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 ...
Gaurang Tandon's user avatar
8 votes
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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 ...
Soumik Das's user avatar
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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 ...
Waylander's user avatar
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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 ...
Nilay Ghosh's user avatar
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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{...
Waylander's user avatar
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7 votes
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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 ...
Oscar Lanzi's user avatar
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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 ...
Dr.Sankalan Mondal's user avatar
6 votes
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Hyperconjugation in cresol

Above are the resonance forms of m-cresol after deprotonation. As you can see, the negative charge resonates around the aryl ring, but never resides on the carbon directly bonded to the methyl group ...
Ava's user avatar
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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 ...
S R Maiti's user avatar
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6 votes
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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 ...
Waylander's user avatar
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6 votes
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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{...
Buttonwood's user avatar
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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 ...
Oscar Lanzi's user avatar
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6 votes
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What is the difference between 2,6-di-tert-butyl-4-methylphenol and 3,5-di-tert-butyl-4-methylphenol 1H NMR spectra?

Indeed the shifts and integrals match up with those reported for butylated hydroxytoluene (BHT), a very common antioxidant used as a preservative, see for instance the list of NMR chemical shifts of ...
Buck Thorn's user avatar
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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 ...
shre_sudh_97's user avatar
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, ...
Nilay Ghosh's user avatar
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5 votes

What is the order of acidic strength among phenol, catechol, resorcinol and hydroquinone?

A quick search on says that resorcinol is more acidic that catechol, followed by phenol. Hydroquinone - strong +M effect and weak -I effect Phenol - the normal resonance you'd expect in all phenols ...
Eashaan Godbole's user avatar
5 votes
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Strong activation of phenoxide ion compared to others

I assume by your notes that your teacher was mentioning electrophilic aromatic substitution reactions. These are two-step reactions. The product-determining step (whether it is ortho-, meta- or para-)...
Mathew Mahindaratne's user avatar

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