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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2
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1answer
74 views

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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0answers
30 views

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 ...
2
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0answers
37 views

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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1answer
43 views

How is phenolic resin made? [closed]

The following chemical structure is phenolic resin. How is this chemical made?
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1answer
38 views

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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0answers
29 views

Why does 1,2-dihydroxybenzene have higher boiling point than monohydroxybenzene? [duplicate]

I studied that any kind of dihydroxybenzene has higher boiling point than monohydroxybenzene, and among the dihydroxybenzenes, I understood that because of inter molecular hydrogen bonding they have ...
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26 views

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 ...
8
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1answer
165 views

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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1answer
78 views

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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1answer
290 views

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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2answers
386 views

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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1answer
928 views

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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0answers
49 views

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 ...
4
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2answers
1k views

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 ...
2
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1answer
213 views

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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1answer
166 views

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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1answer
98 views

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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3answers
878 views

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 $\...
5
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1answer
182 views

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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122 views

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 ...
8
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1answer
2k 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
314 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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3answers
1k views

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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1answer
3k 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
104 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 ...
5
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3answers
5k 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 that the ...
5
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1answer
304 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 ...
3
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1answer
378 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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608 views

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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2answers
2k 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
74 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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842 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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0answers
859 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 ...
2
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0answers
180 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
48 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
3k 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
891 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
4k 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
1k 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 ...
2
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2answers
410 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
4k 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 ...
2
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1answer
948 views

Strong activation of phenoxide ion compared to others

I was told that in phenoxide ion, benzene ring is very strongly activated. The order my teacher told me was phenol < amine < $2^\circ$-amine < $3^\circ$-amine < phenoxide (for activation ...
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1answer
304 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
414 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 by $\ce{...
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2answers
6k 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
31k 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 $\ce{H2O}$)?