Questions tagged [electrophilic-substitution]

Filter by
Sorted by
Tagged with
2
votes
1answer
44 views

Reimer-Tiemann reaction on indole

According to me net reaction should be at $\ce{C3}$ when Reimer-Tiemann reaction is done on indole (see image), since in the resonance structure, negative charge is on this carbon. But, the answer ...
1
vote
1answer
57 views

Validity of the leveling effect of water in nitration reactions

Wikipedia gives this as the levelling effect of water Any acid that is stronger than $\ce{H3O+}$ reacts with $\ce{H2O}$ to form $\ce{H3O+}$. Therefore, no acid stronger than $\ce{H3O+}$ exists in $\...
1
vote
1answer
33 views

Directing effect in Intramolecular Friedel Crafts Alkylation

This reaction should cause ring closure at either the $o-$ or $p-$ position relative to the methyl substituent on the ring (as methyl is an $o,p-$directing group), giving the following products: The ...
1
vote
0answers
23 views

Explanation of the third ortho effect

The third ortho effect is, according to Wikipedia, the phenomenon where in a ring with a meta and an ortho-para director both meta to each other has the incoming nucleophile go ortho to the meta ...
0
votes
1answer
30 views

How does a halogen react in an electrophilic substitution reaction

From what I understand, electrophiles are electron deficient and therefore would be attracted to the electron-rich benzene ring. So would the correct answer be A?
5
votes
1answer
67 views

Solvent Effects in Friedel–Crafts Reaction

While reading about the factors affecting the product of Friedel–Crafts acylation with acetyl chloride, I came across a reaction involving napthalene in two different solvents: in nitrobenzene ...
0
votes
1answer
86 views

Is m-cresol or p-cresol more reactive towards electrophilic substitution?

Which is more reactive towards electrophilic substitution, meta-cresol or para-cresol? Both oxygen and methyl are activating groups. I don't know on what basis do I compare their reactivity. There's ...
5
votes
1answer
207 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 ...
2
votes
1answer
40 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
votes
1answer
117 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.
1
vote
1answer
56 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 ...
5
votes
1answer
281 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
vote
1answer
201 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 ...
-1
votes
1answer
620 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 ...
1
vote
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 ...
0
votes
0answers
40 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 ...
2
votes
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 ...
2
votes
0answers
266 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-...
1
vote
1answer
194 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 ...
0
votes
0answers
72 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 ...
0
votes
0answers
86 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
0
votes
1answer
930 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 ...
0
votes
2answers
321 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 ...
-1
votes
2answers
4k 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 ...