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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Structure of hydroquinone-SO2 clathrate
I've been looking all over the internet for the structure of hydroquinone-SO2 clathrate, but couldn't find anything. I found structures of hydroquinone clathrates with different guest molecules, but I ...
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Association constants of α-cyclodextrin with phenols
I have an exercise that asks me to reason the why for the association constants of a α-cyclodextrin with the guest.
The higher the K the higher the stability of the complex, but I don't quite ...
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Concentration of H2SO4 used in the preparation of phenol from cumene
My professor told that the intermediate, cumene hydroperoxide is converted to phenol by treating it with concentrated sulphuric acid, however my textbook tells me to use dilute acid.
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What is the role of AlCl3 in dealkylation of phenol ring substituted with tertiary butyl?
I was going through the dealkylation reaction of the benzene ring substituted with tertiary butyl and was wondering what is the role of AlCl3 in this?
Here are the details -
During electrophilic ...
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Ring activating substiuents [closed]
Why is phenylamine more electron rich compared to phenol? How does the $\mathrm{NH}_2$ group increase the electron density of the benzene ring more than the OH?
Additionally, why does a negative ...
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Phenol reaction with nitration mixture
When phenol is reacted with nitration mixture my teacher said that picric acid as minor product and a major oxidation product. Is that oxidation product benzoquinone or anything else?
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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 ...
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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?
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 ...
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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 ...
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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 ...
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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{-...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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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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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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 (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 ...
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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 ...
user95393
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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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