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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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Does catechol give Tollens’ test?

Do hydroquinones like catechol or p-hydroxyphenol give Tollens’ test? I know that β-diketones can reduce Tollens’ reagent to give a “silver mirror”, so I would guess that due to tautomerization ...
KMT's user avatar
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-3 votes
0 answers
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Which are the reactions of diphenyl ether and p-phenylphenol as byproducts from phenol manufacture dow's process? [duplicate]

How are these compounds side produced?
Luis Alberto Lozada's user avatar
6 votes
1 answer
350 views

What is the difference between 2,6-di-tert-butyl-4-methylphenol and 3,5-di-tert-butyl-4-methylphenol 1H NMR spectra?

So there was this exercise in my book (picture below) a compound I got to the conclusion that the compound might be either 2,6-di-tert-butyl-4-methylphenol or 3,5-di-tert-butyl-4-methylphenol. I was ...
Roxtron's user avatar
  • 105
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0 answers
76 views

Why is picric acid not more steam volatile than p-nitrophenol, if intramolecular bonding results in increased steam volatility?

I understand that relative to p-nitrophenol, o-nitrophenol would be more steam volatile (as p-nitrophenol can form intermolecular hydrogen bonds), but my question lies in the fact that its volatile ...
rania h's user avatar
0 votes
0 answers
75 views

Steglich Esterification in Alkyl Gallates

Based on my research (reading some articles), some alkyl gallate syntheses used Steglich esterification instead of the usual esterification (Fischer esterification). The reason why Steglich ...
Jonathan's user avatar
  • 155
2 votes
1 answer
153 views

Why can't picric acid be made more acidic by adding nitro groups at the meta positions?

I understand that picric acid is acidic because of the $\ce{-NO2}$ electron withdrawing group, but why can't we add more of those on the meta positions to make it more acidic? Is it because that $\ce{-...
User10001010001000's user avatar
0 votes
0 answers
177 views

Why is m-fluorophenol less acidic than m-chlorophenol?

Why is m-Fluorophenol less acidic than all the other m-Halophenols, even though it has the most inductive effect The data is from : A guidebook to Mechanism in organic chemistry for the JEE, 6th ...
Sai Kritik .T.V's user avatar
-2 votes
1 answer
124 views

How does polarity increase when electron density in oxygen decreases when comparing acidity

My book says the following statement: Due to the higher electronegativity of $sp^{2}$ hybridized carbon of phenol , the electron density in oxygen decreases. This increases polarity of O-H bond and ...
Razz's user avatar
  • 137
2 votes
0 answers
105 views

Predict the products of organic reaction sequence

This is a reaction sequence involving alcohols, phenols, halides, alkenes ,alkanes etc , and the task is to identify all the compounds A to E The few things I was able to identify : The compound C ...
satvik's user avatar
  • 21
5 votes
1 answer
271 views

Does boric acid really rearrange phenols?

This reaction was on prepchem.com and I want to know whether it could work. Most of their reactions are well sourced but this is rather scant (and can't find the patent referenced). It is possible ...
TWiz's user avatar
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2 votes
0 answers
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Reduction of gingerol content in ginger using kitchen equipment

The single topic that this question focuses on is - how to remove gingerol and only gingerol from a piece of ginger in a manner that it remains safe to eat using equipment found in a well stocked ...
Ponder Stibbons's user avatar
0 votes
1 answer
270 views

How does phenol show tautomerism?

I read that atleast one alpha carbon has to be sp3 wrt the functional group (and has to have atleast 1 alpha Hydrogen atom) for it to show tautomerism. I am able to see that in the keto isomers of ...
Zeit Shpaga's user avatar
0 votes
1 answer
122 views

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"
Sajad Khanlarkhani's user avatar
3 votes
0 answers
80 views

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 ...
Lost Anisole's user avatar
0 votes
0 answers
186 views

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 ...
user avatar
0 votes
0 answers
706 views

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 ...
Gallus's user avatar
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1 vote
0 answers
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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 ...
Inkman's user avatar
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0 votes
0 answers
206 views

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 ...
Deepak Arya's user avatar
-5 votes
1 answer
63 views

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 ...
Boson's user avatar
  • 115
3 votes
2 answers
402 views

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 ...
Raviraj Bhosale's user avatar
7 votes
2 answers
505 views

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 ...
C_Lycoris's user avatar
  • 608
8 votes
1 answer
823 views

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 ...
V.G's user avatar
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4 votes
2 answers
347 views

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 ...
ljm's user avatar
  • 151
4 votes
1 answer
2k views

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 ...
harry's user avatar
  • 1,134
2 votes
1 answer
591 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 ...
rev0's user avatar
  • 121
2 votes
2 answers
382 views

Intermediates in aqueous bromination of phenol

A question in my book (an archive for IIT JEE exam questions) asks: In the reaction: The intermediate(s) is/are? The correct answers are given as However, as per my knowledge, compound (b) does not ...
Hridai Khurana's user avatar
2 votes
0 answers
142 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, ...
andrewH's user avatar
  • 167
-3 votes
1 answer
107 views

How is phenolic resin made? [closed]

The following chemical structure is phenolic resin. How is this chemical made?
JustBeingHelpful's user avatar
0 votes
1 answer
274 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 ...
Juan Perez's user avatar
2 votes
0 answers
745 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 ...
Apurvium's user avatar
  • 1,272
10 votes
1 answer
594 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 ...
V.G's user avatar
  • 1,251
2 votes
0 answers
134 views

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 ...
Aman Nambisan's user avatar
8 votes
0 answers
87 views

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 ...
FriendlyGlove's user avatar
5 votes
0 answers
112 views

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. ...
rumtscho's user avatar
  • 478
0 votes
1 answer
407 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?
Niescte's user avatar
  • 65
-1 votes
1 answer
1k 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/...
Yashwini's user avatar
0 votes
2 answers
2k 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 ...
user avatar
3 votes
2 answers
8k 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 ...
Parteek's user avatar
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1 vote
0 answers
143 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 ...
Shreyansh Pachauri's user avatar
4 votes
2 answers
2k 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 ...
zombie's user avatar
  • 71
4 votes
1 answer
2k 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 ...
Cyclopropane's user avatar
  • 2,069
1 vote
1 answer
671 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 ...
Boo's user avatar
  • 71
-1 votes
1 answer
539 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. ...
Fuad's user avatar
  • 1
-1 votes
3 answers
2k 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?
Aniruddha Deb's user avatar
1 vote
0 answers
167 views

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 $\...
Anne's user avatar
  • 49
6 votes
1 answer
1k 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 ...
cjperkie's user avatar
5 votes
1 answer
449 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 ...
Rajat Sansaniwal's user avatar
9 votes
1 answer
4k 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 ...
Denner Evaristo's user avatar
3 votes
1 answer
403 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 ...
user avatar
9 votes
3 answers
3k 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 ...
QuestionCookie's user avatar