Skip to main content

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.

Filter by
Sorted by
Tagged with
5 votes
1 answer
455 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 ...
4 votes
0 answers
68 views

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 ...
6 votes
1 answer
355 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 ...
11 votes
1 answer
831 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 [.....
0 votes
0 answers
77 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 ...
16 votes
1 answer
54k views

What is the product of the chemical reaction between phenol and ferric chloride?

The chemical reaction between phenol and ferric chloride is a test for the presence of phenol. They react with each other to produce a violet complex. However, the reaction is given differently in ...
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 ...
27 votes
2 answers
5k views

Electrophilic Aromatic Substitution: Are protonated OH-groups ortho-/para- or meta-directing?

In Electrophilic Aromatic Substitution ($\text{S}_{\text{E}}\text{Ar}$) reactions groups that can donate an electron pair into the aromatic ring, e.g. $\ce{-OH}$ or $\ce{-NH2}$, are ortho-/para-...
2 votes
1 answer
155 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{-...
0 votes
0 answers
182 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 ...
-2 votes
1 answer
135 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 ...
2 votes
2 answers
392 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 ...
2 votes
0 answers
107 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 ...
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 ...
3 votes
2 answers
410 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 ...
1 vote
1 answer
7k 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). ...
2 votes
1 answer
11k 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 ...
5 votes
1 answer
274 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 ...
2 votes
0 answers
105 views

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 ...
1 vote
1 answer
2k views

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 ...
0 votes
1 answer
282 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 ...
16 votes
3 answers
42k views

Friedel–Crafts reaction of phenol

Does phenol undergo Friedel–Crafts reactions or does it react with Lewis acids like aniline does?
1 vote
0 answers
239 views

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 ...
0 votes
1 answer
126 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"
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 ...
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 ...
0 votes
0 answers
187 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 ...
26 votes
4 answers
45k views

Why is acetic acid more acidic than phenol?

Acetic acid (ethanoic acid, $\mathrm pK_\mathrm a \approx 5$) is more acidic than phenol ($\mathrm pK_\mathrm a \approx 10$), which is reflected in their reactivity with a weak base such as sodium ...
0 votes
0 answers
707 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 ...
0 votes
0 answers
211 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 ...
-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 ...
11 votes
3 answers
12k views

Inductive vs resonance effects and the acidity of phenol

A lot of people rationalize the acidity of phenol by saying that resonance is responsible for much of phenol's acidity as opposed to aliphatic alcohols. However, this image suggests that in fact the ...
7 votes
2 answers
506 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 ...
8 votes
1 answer
828 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 ...
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 ...
4 votes
2 answers
351 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 ...
6 votes
4 answers
8k views

How are phenols made?

What is the equation and conditions for the synthesis of phenols? Would it work if we added $\ce{NaOH}$ to benzene and then refluxed?
2 votes
1 answer
602 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 ...
2 votes
0 answers
149 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, ...
1 vote
1 answer
42k 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 $\ce{H2O}$)?
-3 votes
1 answer
108 views

How is phenolic resin made? [closed]

The following chemical structure is phenolic resin. How is this chemical made?
0 votes
1 answer
277 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 ...
7 votes
2 answers
8k 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. ...
10 votes
1 answer
607 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 ...
2 votes
0 answers
758 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 ...
2 votes
0 answers
153 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 ...
8 votes
0 answers
89 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 ...
2 votes
1 answer
1k 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 ...
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 ...
3 votes
2 answers
2k 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 ...