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Questions tagged [electrophilic-substitution]

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The mechanism of separating AlCl3 [closed]

For this question I have gotten to: I know I am supposed to separate the $\ce{AlCl3}$ through aqueous work up, but I am not sure what the mechanism is. The resulting answer is the enol/keto form + $\...
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1answer
117 views

Electrophilic substitution of benzene with conc. HNO₃ and HNO₂

The following question was given in my FIITJEE study material: $$\ce{Benzene + \text{conc.} HNO_3 + HNO_2 ->}$$ Final product of the reaction is: , , , I started with the solution by deciding ...
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1answer
27 views

Effect of chloromethyl substituent vs methyl substituent on yields of nitration

The effects of $\ce {-CH3}$ and $\ce {-CCl3}$ substituents on the product distribution of an electrophilic aromatic substitution reaction are unambiguous. The $\ce {-CH3}$ group exhibits a clear ...
3
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1answer
79 views

Lactone acylation

Can anyone propose/draw a mechanism for Method A, below, from this paper? Almost all other literature use method B and reagents such as SOCl2.
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1answer
46 views

Can anyone please help me how do you determine kinetically the fastest product of sulphonation of $\beta$ napthol?

I was asked a question in a paper where I was asked to identify the kinetically fastest product of sulphonation of $\beta$ naphthol. Can anyone please help me how do you determine kinetically the ...
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1answer
164 views

Why is formyl chloride unstable while higher acyl chlorides are stable?

Source: Paula Bruice Ed. 2017 Pg.877 From this excerpt, we infer that formyl chloride is unstable. But how does that affect the reaction in any way? Is it just mentioned as a point to note or does it ...
1
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1answer
117 views

When does ipso attack occur in electrophilic aromatic substitution?

My textbook doesn't mention the conditions required for an ipso attack to occur. It just describes some examples where groups like $\ce{-C(CH3)}$ and $\ce{-SO3H}$ are replaced by $\ce{Br}$ using ...
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1answer
293 views

Nitrobenzene - Aromatic Substitution Reactions

Which EAS (electrophilic aromatic substitution) reactions does nitrobenzene show? We know that nitrobenzene is particularly deactivated towards most such reactions, as the nitro group is strongly ...
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0answers
37 views

Find the increasing order of formation of ortho product

Find the increasing order of ortho product formation when Y is (i) F, (ii) Cl, (iii) Br, (iv) I. We know that halides are ortho, para directing for EAS reactions and we consider the electronic ...
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31 views

Distinguishing between a nucleophilic substitution and an electrophilic substitution

Why don't we consider all nucleophilic substitution reactions as electrophilic reactions and vice versa? For example, look at this reaction I found in my textbook. (See picture) This is an ...
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0answers
27 views

Isoptope effect on electrophilic aromatic substitution

My book reads Sulphonation will be the most effected electrophilic aromatic substitution reaction when benzene is replaced by hexadeutrobenzene. I am not able to figure out how. All EAS reactions ...
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168 views

Kinetic and thermodynamic control of sulphonation of toluene

Sulfonation of toluene with conc. $\ce{H2SO4}$ at room temperature gives ortho- and para-toluenesulphonic acid (with $95 \%$ yield), whereas sulfonation of toluene with conc. $\ce{H2SO4}$ at $\pu{150-...
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1answer
116 views

Reaction between phenylamine and halogens

I understand that phenylamine is considerably more reactive than benzene, meaning that it is able to react with bromine water to give 2,3,6-tribromophenylamine. But I was then wondering why I haven't ...
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43 views

Confusion about orienting effects in o-chlorotoluene

I'm confused about where the next substituent in the electrophilic substitution of o-chlorotoluene will land. My question comes on the background of having 3 different sources of information that say ...
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77 views

Attack of 3-methylbutan-1-ol on benzene in acidic medium

That's how I proceeded with the question. However the answer is tert-butylbenzene. I can't figure out why do I have an extra carbon atom. SOURCE - JEE Advanced 1994
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1answer
455 views

Which of the following compounds will form significant amounts of meta product during mono-nitration reaction? [closed]

Hi, I tried to answer this question based wholly on the concepts of inductive effects. But haven't gotten anywhere with it. I would appreciate any help regarding these questions: What condition ...
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2answers
204 views

Which is more activating among Phenol, Sodium Phenoxide & Anisole? Also arrange them in increasing order of their activating effect

This is in reference to Kolbe's Reaction, actually I think that Sodium Phenoxide is the most activating because, in Kolbe's Reaction we don't make react $\ce{CO2}$ directly with phenol for the ...
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2answers
3k views

Effect of nitro group basicity order of o,m and p nitroanilines?

Would someone please help me with this? The order of basicity of o,m and p nitroanilines is m>o>p. My book states that ortho isomer has -I effect, -M effect as well as ortho effect, and meta isomer ...