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Questions tagged [phenols]

Use this tag for questions about phenols, their synthesis, analysis, properties and more. Do not use the 'alcohols' tag for phenols due to the differences between the two classes.

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23 views

Why are meta-sustituted phenols more acidic than phenol? [on hold]

We have been taught that electron donating groups reduce the acidic nature of phenols and its derivatives. Then why are all the following compounds more acidic than phenol:
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1answer
136 views

What is the mechanism of oxidation of phenol to benzoquinone?

I looked up the mechanism in a lot of organic chemistry books, including Clayden, Klein, Solomons, McMurry but I couldn't find the mechanism of oxidation of a phenol. I also looked it up in ...
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1answer
58 views

Which compounds react positively in the aniline dye test?

I read that to test for the presence of phenol groups in an organic compound the aniline dye test can be performed. If the solution has phenol present it gives a red or orange precipitate to confirm ...
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1answer
187 views

what is mechanism for reaction phenol + dimethylsulphate -> anisole

Dimethyl sulphate breaks the oh bond and forms anisole. How does the reaction proceed?? is it oxygen lone pair attacks on sulphur which has partial positive charge?? the reaction takes place in ...
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3answers
82 views

Extraction between cyanex 923 and phenol

I want to remove phenol from wastewater so I used the cyanex923 as an extractant or carrier to extract phenol from the wastewater (the name of the process is non-dispersive solvent extraction) but the ...
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3answers
1k views

Why does the -OH group in β-naphthol direct the incoming diazonium salt towards the ortho position? [duplicate]

In the following reactions, the major product W is I was doing this question which asks me the product of a diazotisation coupling reaction between diazonium chloride and β-naphthol. I know ...
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1answer
99 views

Partial oxidation of toluene

While reading the preparation of phenol from cumene by reaction with $\ce{H2O2}$ or partial oxidation, I was curious to find out why toluene wasn't used. I checked the literature and found that ...
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1answer
100 views

Equilibrium Constants For Phenol Tautomers

I encountered the following equilibrium constant values for the keto-enol interconversions of phenol in Organic Chemistry (Solomons, Fryhle, Snyder, 3rd Edition): I wonder what could explain the ...
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105 views

Diazo Coupling reaction with para substituted phenol?

Usually Diazo coupling occurs at para position until the para position is occupied , in which case coupling occurs at ortho position . While solving questions I found in both the cases as shown , ...
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2answers
561 views

Reaction of orthocresol with butyrolactone in presence of AlCl3 and heat

What will be the major product of the following reaction? Please also help me with the mechanism. I'm not sure whether C- acylation or O- acylation will occur here. And if O- acylation does occur, I ...
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1answer
63 views

Can benzene ring be the part of a acyl group

Can benzene ring attached to c=o i.e carbonyl group be considered as a acyl group?
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361 views

Mechanism of oxidation of phenol to quinone by chromium(VI)

In the supplementary information for Org. Lett. 2005, 7 (19), 4297–4300, the following experimental method for the synthesis of 2-bromo-6-methylcyclohexa-2,5-diene-1,4-dione is given: To a ...
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531 views

Converting phenol to para-nitrophenol via nitrosophenol

Our class 12 text book says that if we treat phenol with mixture of concentrated $\ce HNO_3$ and $\ce H_2SO_4$, instead of nitration, the ring is oxidized to quinone. So, the book proposes that we ...
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132 views

Addition of NaBH4 and LiAlH4

NaBH4 and LiAlH4 will be a source for the hydride ion and reaction will begin with addition of hydride by displacing the carbonyl group. But I am not sure will it attack both the carbonyl or only one....
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1answer
41 views

Are polyhydroquinones considered to be polyphenols?

Looking at the Wikipedia article for polyphenol, I was struck by how the monomer units shown are all substituted meta or ortho for the hydroxyl groups. https://en.wikipedia.org/wiki/Polyphenol#...
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1answer
1k views

Reaction of chloroform, resorcinol and strong base

A common reaction used to identify resorcinol (benzene-1,3-diol) in the laboratory is to react it with chloroform in presence of 30% sodium hydroxide (NaOH). A red coloured solution (or precipitate) ...
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2answers
410 views

Phenol and Deuterated Sulphuric Acid

What happens when phenol reacts with $\ce{D2SO4}$ in presence of $\ce{D2O}$? How many hydrogens in total are replaced by deuterium? Is the hydrogen of the hydroxyl group and three hydrogens ortho ...
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1answer
2k views

Reactivity comparison of phenol and toluene towards electrophilic substitution

Which aromatic compound is more reactive towards electrophilic substitution? benzene chlorobenzene phenol toluene Correct answer: phenol But, according to me, the answer should ...
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2answers
447 views

How to determine the order of acidity of the following dimethyl nitrophenols

This is how I went about it, although I got a wrong answer: 3,5-Dimethyl-4-nitrophenol (2) shows the nitro group to be sterically hindered, due to which it should go out of plane and this will be an ...
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2answers
206 views

Out of the given reagents, find the ones to be used to convert benzene to p-aminophenol

$\ce{Br2/FeBr3}$ $\ce{CH3Cl/AlCl3}$ $\ce{KMnO4}$ $\ce{HNO3/H2SO4}$ $\ce{NBS}$/hv $\ce{NaOH}$ $\ce{Sn/HCl}$ $\ce{NH4SH}$ $\ce{NaBH4}$ I'm able to get the amino group onto the ring by using 4 and 7. ...
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1answer
2k views

Reaction between phenol and nitrous acid

My question is about the products formed when phenol reacts with nitrous acid. I googled it and reached this PubChem paper (DOI: 10.1016/S0045-6535(02)00857-3), which states: It was found that ...
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1answer
414 views

Strong activation of phenoxide ion compared to others

I was told that that in phenoxide ion, benzene ring is very strongly activated. The order my teacher told me was phenol < amine < 2 degree amine < 3 degree amine < phenoxide (for ...
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1answer
237 views

reimer tieman reaction only one ortho product [closed]

why we cannot have two reimer tiemann substitutions on the same phenol as CHO- group is electron withdrawing it wont disturb electron concentration at its meta which is phenol's ortho- product
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1answer
178 views

Reaction of carbonyl cyclic diene with Grignard reagent

Predict the major product of this reaction: The two compounds on the right are the possibilities that I thought of (weren't given in the question). According to me: attack on carbonyl carbon ...
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2answers
3k views

Phenol preparation from Grignard reagent

Reaction: Phenyl magnesium bromide in presence of excess oxygen, on acidification yields phenol, as below. My instructor told me that the above reaction occurs, and if the reagent is in excess then ...
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1answer
16k views

Halogenation of Phenol [closed]

Why does only one $\ce{Br+}$ ion get generated in a non-polar solvent (such as $\ce{CS2}$), while more $\ce{Br+}$ ions are generated in aqueous or polar solvent (such as $\ce{H2O}$)?
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Reaction of phenol and zinc dust

There is a reduction reaction of phenol with zinc dust which is found in many books. $\ce{Ph-OH + Zn -> Benzene + ZnO}$ However, a simple google search fails to explain anything about the ...
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1answer
4k views

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

This question is from a book that gives the answer as $$ \text{hydroquinone} < \text{resorcinol} < \text{phenol} < \text{catechol} $$ but does not provide any explanation for the answer. If ...
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3k views

Why is phenol more acidic than aniline?

I find that there are two contradicting factors at play here: 1) On removing proton, negative charge on oxygen is more stable than it is on nitrogen (because of greater electronegativity of oxygen). ...
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2answers
3k views

Reimer–Tiemann-like reaction of catechol with diiodomethane

I have studied the Reimer–Tiemann reaction of phenol with chloroform in presence of aqueous strong alkali. It takes place with intermediate dichlorocarbene. I have also studied the Reimer–Tiemann "...
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1answer
160 views

Why does orthocresol behave as a skin irritant?

o-Cresol or ortho-Cresol or 2-methylphenol is a constituent of tobacco smoke, and, like most other phenols, behaves as a skin irritant, causing a burning sensation when it comes in direct contact, or ...
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515 views

Why does phenol react on oxygen in the Gattermann–Koch reaction?

When discussing the Gattermann–Koch reaction on phenol substrates, it has been said that O-acylation is a problematic competing reaction as in a phenol, there's high electron density on the O atom [...
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1k views

Why is o-fluorophenol a stronger acid than p-fluorophenol?

The $\mathrm{p}K_\mathrm{a}$ value of o-fluorophenol is $8.7$, while that of the p-fluorophenol is $9.9$. It's obvious that the inductive effect is more dominant at ortho-position, which results in a ...
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2answers
3k views

Hyperconjugation in cresol

In cresol both $+I$ effect as well as hyperconjugation work together to determine its acidity. When the methyl group is present in the ortho- and para-position both of them can act upon phenol. ...
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2answers
7k views

Can phenol be detected with a ceric ammonium nitrate test?

Today, I came across a question which asked name three reagents can be used for identification of phenol. The answer given was: Neutral $\ce{FeCl3}$ $\ce{ NaNO2 +HCl}$ $\ce {(NH4)2[Ce(NO3)...
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1answer
2k views

Phenol smell from hands

It is a question which I faced when I was in Senior year in high school, I used my hands to handle phenol which has turned pink due to oxidation, I washed my hands with all kind of soaps but smell in ...
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2answers
683 views

Between 3-chlorophenol and 3-fluorophenol, which one is more acidic?

Between 3-chlorophenol and 3-fluorophenol, which one is more acidic? In this case, I know that both F and Cl are electron-donating groups. Furthermore, I know that F is more electron-donating than ...
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2answers
212 views

How is rotenone a polyphenol?

How is it a polyphenol if it doesn't have a hydroxyl group? If it isn't which subclass would you put it in, and which functional groups does it contain?
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193 views

Why did phenol respond to Brady's reagent?

I was teaching a friend a few basic organic analysis experiments, during which I was showing him, how to get an alcohol, and took a sample of phenol. The neutral $\ce{FeCl3}$ test went fine(which i ...
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3answers
498 views

Is there an intramolecular hydrogen bond in guaiacol?

Is there a hydrogen bond between the $\ce{H}$ atom of $\ce{-OH}$ group and the $\ce{O}$ atom of the $\ce{-OCH3}$ group in ortho-methoxyphenol? I was told no. But I want to know why.
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Evaluation of a synthesis from aspirin to paracetamol from YouTube

Recently the YouTube chemist Nile Red performed an interesting conversion from aspirin to paracetamol (Link: https://www.youtube.com/watch?v=YPIr26-Tg5c), using the following steps: He performed the ...
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1answer
136 views

Can alkyl-substituted phenols be reduced to alkyl-substituted benzenes by zinc dust?

I know that phenol can be reduced to benzene by distilling it with zinc dust. But I want to know if that concept can be expanded. E.g., take chavicol or 4-(prop-2-en-1-yl)phenol; could you still ...
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2answers
277 views

Organic problem: acidity of benzene substituents

Ortho nitro benzoic acid is more acidic than para benzoic acid since intermolecular H bonding comes into play in the latter compound. But why is that among para nitro phenol and ortho nitro phenol, ...
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1answer
5k views

Which Phenols give the colours blue, green or violet in the neutral FeCl3 test?

I have read about the neutral FeCl3 test for Phenols, where a positive test is indicated by the colour of the solution which ranges from green to blue to violet. But which specific derivatives of ...
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1answer
3k views

Is picric acid a very strong acid?

Picric acid has nitro groups in para and ortho positions, so it has great possibility to go for resonance, thus it is supposed to be a very good acid. But a question arises! The $\ce{O}$ of $\ce{-OH}$...
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1answer
2k views

What is the functionality(reactive sites) of phenol molecule? [closed]

My class 12 chemistry textbook says that phenol molecule has three reactive sites or it's functionality is three. But I am confused whether it is so or not, because, what I know, phenol has three ...
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2answers
19k views

Why o-Nitrophenol is more volatile than p-Nitrophenol? [duplicate]

Why o-Nitrophenol is more steam volatile than p-Nitrophenol?
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708 views

Physical properties of phenols

Order of increasing boiling point is p-nitrophenol > m-nitrophenol > o-nitrophenol. The difference between bp of p- and o-nitrophenol is that one form intermolecular hydrogen bonding while other form ...
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Suggestion for a Synthesis of Paracetamol — plausible?

I have seen a number of different plausible syntheses for paracetamol but they suffer from problems such poor regioselectivity of aromatic substitution (usually when nitrating phenol getting a mixture ...
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Acidity order of nitrophenols

As in other posts I have seen and learnt that, if one is given four compounds, namely para-nitrophenol, ortho-nitrophenol, meta-nitrophenol and phenol and is told to arrange them in order of acidity, ...