Questions tagged [electrophilic-substitution]
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27
questions
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21 views
Trimethylsilyl vs tert-butyl as activating substituent of benzene
Would trimethylsilane as a benzene substituent have an activating effect relative to tert-butyl for electrophilic substitution reactions?
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21 views
Relation between activating properties and directing nature
Why are activating groups not always ortho-para directing and decativating groups meta directing?
For example, we have:
Halogens which are deactivating, but ortho-para directing.
Nitro group which ...
2
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0answers
24 views
How far does the delocalisation (resonance) effects for substituents extend for a conjugated system?
Let's say we have a conjugated system like this one:
Now, the delocalisation of the benzene electrons with the nitrate system means that the ortho, and para positions on the immediate benzene ring ...
2
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1answer
79 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 ...
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1answer
67 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 $\...
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1answer
42 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 ...
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0answers
28 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 ...
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1answer
44 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
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1answer
113 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 ...
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1answer
100 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 ...
6
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1answer
262 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:
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I started with the solution by deciding ...
2
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1answer
49 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
137 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
61 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
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1answer
338 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 ...
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1answer
228 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
739 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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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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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 ...
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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 ...
3
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0answers
316 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
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1answer
209 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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78 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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89 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
973 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
358 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
5k 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 ...
