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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Is formation of cyclic carbonate from trimethyl orthoformate and vicinal aromatic 1,2-diol possible? [closed]

Hello, my question is, "is it possible cyclic carbonate formation between trimethyl orthoformate and vicinal aromatic 1,2-diol"
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Acidification of a vicinal diol [duplicate]

The following is a question from Advanced problems in organic chemistry by MS Chouhan: The options given are: My initial thought was that this could be a pinacol–pinacolone rearrangement. However ...
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Colorimetric titration of bisphenols: Liebermann's reaction?

I would like to titrate the content of bisphenols leeched in hot water from plastic bottles. I was thinking of a colorimetric titration using Lieberman's reaction, which detects phenols. Would the ...
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Help with mechanism: Isomerization of eugenol

I'm confused about the mechanism for the isomerization of the external alkene eugenol to the internal alkene isoeugenol. I've added an image below of their structures. The reaction is usually carried ...
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What are the resulting conjugate acid and base of phenol and 4-nitrophenol

I have to complete the equation 4-nitrophenol + phenol ---> and then label the acid, the base, the conjugate acid and the conjugate base. I think the answer ...
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What is the mechanism when 1-chloro-4-nitrobenzene reacts with NaOH?

The reaction mechanism in my textbook when 1-chloro-4-nitrobenzene reacts with NaOH is given as follows, When chlorobenzene reacts with NaOH the product formed is phenol with benzyne as the reaction ...
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Natural preservatives of ink

Would pure compounds like thymol, carvacrol, and cinnamaldehyde work as preservatives of fountain pen ink? I'm specifically interested in three properties - Prevention of growth (mostly fungal) in ...
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Reaction mechanism of formation of salicylic acid with Phenol and carbon tetrachloride in basic medium?

With classic Reimer-Tiemann reaction a variation is also given in my lecture notes which use carbon tetrachloride instead of chloroform. But to me, it seems like it would be just a substitution ...
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Identifying products [duplicate]

How to determine the major and minor products in a reaction? What factors are useful to do so? For ex: Nitration of phenols, gives the ortho nitro phenol as the the major product and para nitro phenol ...
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Why doesn't the acetic anhydride moeity react with the nucleophilic carbonyl oxygen of salicylic acid?

I know that salicylic acid with acetic anhydride under acidic conditions gives acetylsalicylic acid (aspirin). But my question is, why is it that post the protonation of carbonyl oxygen of acetic ...
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Mechanisms for Reimer-Tiemann and Kolbe-Schmidt reaction on deuterium labelled phenol

I was solving a bunch of reactions when I encountered the following: So for the first question: This is a Reimer-Tiemann reaction. I felt that the tautomerism would result in the deuterium getting ...
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Comparing acidic strengths between benzylammonium ion and phenol

Question Compare the acidic stengths between benzylammonium ion and phenol. I first tried to remove the H+ ion from both of them and tried to compare the relative stabilities of resulting conjugate ...
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What does acidity of para-alkyl substituted phenols depend on?

Problem Arrange the following organic compounds in decreasing order of acidity. Answer Question According to my knowledge the answer should be P, Q, R, S. As we proceed from P to S we are ...
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Mechanism of formaldehyde / phenol condensation

The production of bakelite using this method, but with an acid as the catalyst is simple enough; a protonation of the carbonyl oxygen, followed by an electrophilic substitution to the ring. The ...
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Is there a way to convert aniline to phenol without diazotizing it?

I am a high school student and while reading about reactions on amines, I was trying to figure out a way to convert aniline $(\ce{C6H5NH2})$ to phenol $(\ce{C6H5OH})$ without diazotizing it with ...
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Intermediates in aqueous bromination of phenol

A question in my book asks: In the reaction: The intermediate(s) is/are? The correct answers are given as However, as per my knowledge, compound (b) does not appear in the reaction mechanism. Is ...
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DIY lipid nanoparticles

I, and a number of friends, take a bunch of supplements that are polyphenols and often flavin-oids, -ols or -es; also numerous carotenoids. Examples include quercetin, luteolin, fisetin, curcumin, ...
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How is phenolic resin made? [closed]

The following chemical structure is phenolic resin. How is this chemical made?
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Meaning of "Nonyl-phenol 10 mole"

In my workplace we are purchasing "Nonylphenol 10 mole" and "Nonylphenol 30 mole" for use as non-ionic surfactants. At first I assumed, because of the name, that the substance was ...
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Comparison of boiling points of para-derivatives of phenol

The boiling points of four para-derivatives of phenol are: How can we compare the boiling points of p-nitrophenol and p-aminophenol? Apart from the hydroxyl group, p-nitrophenol has two oxygen atoms ...
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Why is quinone mono oxime more stable than 4-nitrosophenol?

When we do nitrosation of phenols, we get para-nitrosophenol as the major product, which tautomerises to quinone mono oxime. This article states that it largely exists in the quinonoid form. My ...
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Which one out of a keto group or a hydroxyl group would get protonated first if both are present in a compound (attachment)

In the solution provided by my teacher he protonated the ketone, moved the +ve above by resonance did methyl shift and then did dehydration to form a benzene type system. Is this only because for this ...
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Mechanism of Hypervalent Iodine Phenolic Coupling

I need some help understanding the hypervalent iodine phenolic coupling reaction taking place in this synthesis of morphine, the reaction uses $\ce{PhI(OAc)2}$ as the hypervalent reagent and ...
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How much oxygen is used up by the browning of an apple?

This is inspired by a recent popular question on Cooking. Let's assume that I take some apples, cut them up, and place them in a hermetically sealed container. Then the container goes into the fridge. ...
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Fries Rearrangement Products

During Fries Rearrangement, oxygen donates its lone pair to $\ce{AlCl_3}$ forming $\ce{-O^+-AlCl3}$. Since this is a strong electron withdrawing group, shouldn't the final product be meta-substituted?
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Phenoquinone vs benzoquinone [closed]

Are phenoquinone and benzoquinone the same thing? When I searched for the colour of benzoquinone I found that it's yellow. But when I searched oxidation of phenol in air. It states that it turns pink/...
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ortho/para-Selectivity in the Reimer-Tiemann Reaction [duplicate]

I can't figure out why the dichlorocarbene molecule produced in the Reimer-Tiemann reaction gets attached to the ortho position of phenol. The ortho position is sterically slightly more hindered due ...
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Why does p-nitrophenol give sodium bicarbonate test, but o-nitrophenol does not?

Both ortho- and para-nitrophenol are less acidic than carbonic acid. But still paranitrophenol reacts with sodium bicarbonate to give carbonic acid and sodium paranitrophenoxide. However, this is not ...
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Will ipso substitution work in both cases of vanillic and isovanillic acids here or not?

What will be the product of the 2 reactions when bromine is taken in excess? I think ipso substitution will work here and there will be two $\ce{Br}$ substituting in both products, but in the book it ...
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Benzene to phenol in a single step

My teacher told me we can convert benzene to phenol within a single step using $\ce{V2O5}$/ $\ce{O2}$ at 300 ⁰C (not 500 ⁰C). Later I searched for that reaction but I couldn't find it in all over ...
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What happens to the NMR of an alcohol when D2O is added?

What difference you expect in the 1H NMR spectrum of phenol in $\ce{CDCl3}$ after a drop of $\ce{D2O}$ is added to the test tube? 1) Since the $\ce{-OH}$ of the phenol is quite acidic, it undergoes ...
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Why does cinnamaldehyde pass the ferric chloride test?

I was given some data to determine what the unknown compound was and figured out that it was cinnamaldehyde. After reviewing the classification test given to me by my professor, I was a bit confused ...
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Are Phenol and Alchohol both hydrocarbons? [closed]

In many books there are said that Alchohols are hydrocarbons, and some says they are not. On the other hand Phenols are said aromatic hydrocarbons. It is well known that Phenols are not Alchohol. ...
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Acidity order of o-nitrophenol vs. o-chlorophenol [closed]

It is given that the above statement is true. Why does o-nitrophenol, in spite of intramolecular hydrogen bonding, have a lower $\mathrm{p}K_\mathrm{a}$ than o-chlorophenol?
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How does the relative acidity of 2,3-dinitrophenol compare to that of 2,4-dinitrophenol?

I am assuming that the -I inductive effect in 2,3-dinitrophenol is stronger than in 2,4-dinitrophenol since it operates through less bonds, therefore on inductive grounds it should have a lower $\...
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pKa of phenols using UV-Vis spectroscopy

I have done an experiment where I dissolved four different substituted phenols in acidic, basic, and buffer solutions, and recorded the UV-Vis spectra for each. I'm supposed to pick a wavelength where ...
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Acidic strength of phenol derivatives

While comparing the strengths of o-nitrophenol and p-nitrophenol, p-nitrophenol is found to be more acidic. The reason I studied for this is $\ce{H}$-bonding in o-nitrophenol which makes the acid more ...
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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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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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8 votes
3 answers
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Reaction mechanism of rearrangement

I am currently studying for my organic chemistry exam, but there is one problem I do not understand. Unfortunately, I do not have any solutions. See image for the problem. My first thought was the ...
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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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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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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 that the ...
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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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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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Diazo Coupling reaction with para-substituted phenol?

Usually Diazo coupling occurs at para-position unless the para-position is occupied, in which case coupling occurs at ortho-position. While solving questions I found in both the cases as shown, the ...
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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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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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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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Can we convert phenol to para-nitrophenol via nitrosophenol?

Our class 12 text book says that if we treat phenol with mixture of concentrated $\ce {HNO3}$ and $\ce{H_2SO_4}$, instead of nitration, the ring is oxidized to quinone. So, the book proposes that we ...