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Questions tagged [electrophilic-substitution]

use for reactions where an electrophile (electron-deficient species) displaces a substituent. Reactions like nitration fall under this category

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Nonplanar polarization in allenes and aromatic compounds

I recently came across this elaborate article on electrophilic aromatic subsitution. In the third chapter "General mechanistic considerations in electrophilic aromatic substitution" the ...
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How many times does substitution happen here?

(This question is from a dubious source) The reaction taking place here is Friedel-Crafts acylation of benzene with 1-chloro 2,2-dimethyl propanone (pivaloyl chloride?). To me, the options seem most ...
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How is nitrogen the most powerful electron donor in aromatic rings?

In Clayden, page 735, Aromatic Heterocycles 1:Reactions: The other simple five-membered heterocycles are furan, with an oxygen atom instead of nitrogen, and thiophene, with a sulfur atom. They also ...
zxen's user avatar
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Major product in chloro-sulfonation of toluene

According to Clayden's Organic Chemistry (2e) (p.485) ... and the acid chloride (tosyl chloride, $\ce{TsCl}$) needed to make tosylates can be made from the acid in the usual way (p. 215) with $\ce{...
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Friedel-Crafts alkylation of fluorochloropropane

Consider benzene reacting with 1-chloro-3-fluoropropane, with $\ce{AlCl3}$ as the Lewis acid. My question is, is this reaction feasible? If so, what is the product formed and do cationic ...
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Is -NR3+ really meta directing? [duplicate]

For electrophilic aromatic substitution, it is said that -NR3+ is meta directing, but since it only shows electron withdrawing inductive effect and inductive effect decreases with distance so it must ...
Garv Chaudha's user avatar
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3 answers
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When does negative charge represent a pair of electrons?

Probably a stupid question but it has been bugging me for quite some time. I was reading Clayden (organic chemistry textbook) and in it, the author gives an example of $\ce{OH-}$ and $\ce{BH4-}$ to ...
Atul Anand's user avatar
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Does nitration of phenol with nitric acid yields 2,6-dinitrophenol?

I've learnt that the $\ce{OH}$ group is 2- and 4-directing, but this has caused some confusion. If $\ce{HNO3}$ reacts with phenol, would there be any 2,6-dinitrophenol produced? I know that the first ...
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Retrosynthesis of 1-(3-chloro-5-nitrophenyl)-2,2-dimethylpropan-1-one

I was tasked with figuring out the order of attaching the functional groups to a benzene ring for the synthesis of 1-(3-chloro-5-nitrophenyl)-2,2-dimethylpropan-1-one: I propose the following order: ...
Zack Eichenbaum's user avatar
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1 answer
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Are there any specific requirements for ipso substitution in aromatic compounds?

In one of the questions in my textbook, (bromine + water) is able to replace the -SO3H group attached to phenol via ipso substitution, but in another question, (bromine + Fe) cannot replace the same ...
Muskaan S's user avatar
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3-Step Transformation to Humulone

I have some ideas on how this transformation may occur. We're currently studying Ch. 3 (Polar Rxn's under Acidic Conditions) from Grossman's book. I've found some data online that shows we can perform ...
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Why is a strongly-ortho directing substituent preferred over a strongly-meta directing substituent?

When we were taught electrophilic aromatic substitution at our school, our teacher made us write the "rules" of di-substituted benzene concerning the decision of the substitution position ...
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What determines whether a mechanism is nucleo/electrophillic addition/substitution?

So I recognise what an electrophile and a nucleophile is, but not all mechanisms (that I know of at least) have one species substituting or adding. For example, propanone added to NaBH$_4$ has an ...
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Internal Electrophilic Aromatic Reaction in 3-chlorobutylbenzene

I recently came across the reaction scheme: Aluminum chloride to 3-chlorobutylbenzene. In Jerry March, reaction scheme is provided for 4-chlorobutylbenzene with $\ce{AlCl3}$ where ring closure occurs ...
Shukraditya Bose's user avatar
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Why does aromatic sulfonation of 3-aminobiphenyl occur at the para position of the adjacent ring?

I know that the amino group $\ce{-NH2}$ is a strong activator, so the sulfonate group $\ce{-SO3H}$ should be directed at the ortho or para position. However, the sulfonation occurs at para position on ...
Adagio_68's user avatar
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Electrophilic substitution on disubstituted benzene, when deactivating groups are at para

As far as I have been able to understand this, the sites of electrophilic substitution are majorly decided on basis of the fact that "Where the electron density is more, electrophilic ...
Gurjot Singh's user avatar
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addition of HBr to a conjugated alkene

here we shift double bond and change the carbocation from 3 degree to 2 degree, by doing so we are saying that hindrance matters more than carbocation stability, is this always the case in such ...
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Electrophilic Substitution of Substituted Benzene

I know that phenol doesn't undergo the Friedel-Crafts Alkylation and Acylation reactions, because the reagent $\ce{AlCl3}$ forms a complex with phenol, as the oxygen atom donates it's lone pair to the ...
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Effect of trifluoromethyl substituent on electrophilic substitution [duplicate]

Problem - Find which carbon is most susceptible to electrophilic attack (among carbons numbered $1$ to $6$): Answer given (may not be the correct one) - My question - $1.$ I know that $\ce{-CCl3}$ ...
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Electrophillic susbtitution of bromine on styrene and cinnamic acid in the presence of FeBr3, a Lewis acid

Bromine gas, in the presence of $\ce{CCl4}$, undergoes on addition reaction at the double bond in both styrene and cinnamic acid, illustrated below. Styrene: Cinnamic acid: Bromination of benzene in ...
Samardeep singh's user avatar
3 votes
0 answers
248 views

About the Vilsmeier-Haack formylation of this compound

I was reading an article and found the following reaction sequence: The second step involves a formylation of the hydrazone with the Vilsmeier reagent to, first synthesize the pyrazole ring and then, ...
Mictlantecuhtli's user avatar
6 votes
2 answers
616 views

Can't aluminium chloride do electrophilic substitution as an electrophile?

In halogenation reactions of benzene, $\ce{AlCl3}$ is used as a catalyst in order to form electrophile $\ce{E^+}$. So I was wondering that $\ce{AlCl3}$ is a Lewis acid (that fact being also used in ...
Yash Agrawal's user avatar
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Competition between aromatic sulphonation and nitration

Say you take a substituted benzene* and react it with oleum and nitric acid. Would it result in a nitrated ring, a sulphonated ring, or some sort of a combination? Thinking about it in terms of the ...
harry's user avatar
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12 votes
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Meta-directing nature of anilinium cations

The comments on this answer seem to detail a trend in which $\ce{NR3+, NHR2+, NH2R+}$ all show meta-directing nature towards electrophilic substitution, with the slightly stronger para-direction of $\...
harry's user avatar
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3 votes
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611 views

Why do resorcinol and iodine react to give 2-iodobenzen-1,3-diol?

I am supposed to perform the above shown reaction in the lab soon, but I don't really understand the mechanism behind it. I got told by my lab assistant that the mechanism is an electrophilic aromatic ...
Anni.Lin's user avatar
5 votes
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419 views

Lack of polysubstitution in Friedel–Crafts t-butylation of phenol

According to our lab manual: In general, Friedel–Crafts alkylation is not employed to make monoalkyl benzene derivatives because of the polysubstitution. But our professor told us that while we are ...
O.Ceren's user avatar
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Why does (2-methoxyethyl)benzene undergo nitration at the ortho position (major product)?

This is an option in a question in which we needed to mark all the correct reactions: According to the answer key, this is a correct option. As an alkyl group is directly bounded to the benzene ring, ...
Pal's user avatar
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Major product of the nitration of benz[cd]indol-2(1H)-one

Decide major product for given reaction of electrophilic aromatic substitution: Is the major product a because of steric hindrance, or is it b because of hydrogen bonding?
Jay's user avatar
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Why doesn't aromatic substitution add at multiple positions in one reaction?

When you do aromatic substitutions, you usually see the major products with one substituent added. My question is why can't you add multiple substituents in one reaction? For example, the image below ...
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Aromatic Substitution in acidic medium

Find product A. I tried solving but why isn't the answer this The answer is given this
PureJokester1007 's user avatar
1 vote
1 answer
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What is the electrophile in Perkin's condensation reaction?

In Perkin's reaction, an aromatic aldehyde reacts with an acid anhydride to give an alpha-beta unsaturated aromatic acid. Which reactant is the electrophile and which one is the nucleophile?
sam's user avatar
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1 answer
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Hell-Volhard-Zelinski Reaction [closed]

What is the role of red phosphorus in hvz reaction? Initially I think that red phosphurus is nothing but a catalyst. But it is not a catalyst.
kunal agarwal's user avatar
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0 answers
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Electrophilic Aromatic substitution reactions of aromatic compounds [closed]

Benzene and substituted benzene (phenols, aromatic ethers, benzaldehyde, aromatic ketones like acetophenone, benzoic acid, aniline and nitrobenzene) generally can undergo electrophilic Aromatic ...
S RM's user avatar
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1 answer
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What happens when FeF3 is reacted with benzene? [closed]

My text book says that halobenzenes can be prepared by aromatic substitution on benzene ring by using Fe or FeX3 as Lewis acid but this method isn't useful for preparation of fluoro benzene because of ...
Anant bansal's user avatar
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The main difference between using AlCl3 and FeCl3 in Friedel-Crafts alkylation

What is the main difference between using $\ce{AlCl3}$ and $\ce{FeCl3}$ in Friedel-Crafts alkylation? Is that $\ce{FeCl3}$ disfavors carbocation rearrangement in Friedel-Crafts alkylation?
Youcef José Fred's user avatar
4 votes
1 answer
1k views

Electrophilic Substitution with Ceric Ammonium Nitrate and Lithium Bromide as reagents

The 2020 IChO Preparatory Problem List (source here) had the following reaction as part of the solution to the first question: (CAN = Ceric Ammonium Nitrate). What is the mechanism for this '...
Aniruddha Deb's user avatar
2 votes
0 answers
391 views

Why don't phenol behave like aniline in electrophilic substitutions?

As far as I know, many electrophilic aromatic substitution reactions fail to undergo the usual way in aniline. This is due to $\ce{-H2N}$ group being basic (pKa of $\ce{NH3}$ = 38), even it is ...
234ff's user avatar
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2 votes
1 answer
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Acids used in Friedel-Crafts alkylation

I am learning adding alkyl groups to benzene using Fridel-Crafts alkylation: I know that it is very common to use $\ce{AlCl3/AlBr3}$ as Lewis acid catalyst in this reaction. But I am just wondering ...
234ff's user avatar
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1 answer
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activating and deactivating groups and directing effect

In electrophilic aromatic substitution: I have just learnt a 'rule' about benzene with more than 1 substituents attached (excluding the effect on steric hindrance): if a strong activating group (EDG) ...
234ff's user avatar
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4 votes
1 answer
855 views

Electrophilic substitution on Borazole

As Borazole ($\ce{B3N3H6}$) is aromatic, it can show electrophilic aromatic substitution. Now, my question is when borazole undergoes electrophilic aromatic substitution reaction, on which atom does ...
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6 votes
1 answer
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Regioselectivity in Electrophilic Aromatic Substitution of Pyrrole and Indole

If we look into the structures of Pyrrole and Indole, they are very similar. Only Indole has one extra Benzene ring attached to it, i.e. if we attach one Benzene ring to Pyrrole, what we'll have is ...
Soumik Das's user avatar
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1 vote
1 answer
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Nitro-substitution [closed]

Here I expected (b) to happen via nucleophilic substitution, but contrary to that (a) is the one occuring. What exactly is happening here?
shreya's user avatar
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1 vote
1 answer
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Steric Effects in Friedel-Crafts Reactions

I recently came across a Friedel-Crafts reaction happening between benzoyl chloride and mesitylene with $\ce{AlCl3}$ as a catalyst. Apparently this reaction doesn't occur due to steric effects even ...
Atharva's user avatar
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2 votes
1 answer
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Which is the major product of bromination of 3-(dimethylamino)benzamide, ortho or para?

I know that A will most probably not happen because of high steric hindrance. However between B and C, will B become the major product? Because $\ce{-N(CH3)2}$ is less bulky compared to $\ce{C=O-NH2}$,...
sara's user avatar
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1 vote
2 answers
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When we cannot use Friedel-Crafts acylation to insert alkyl group?

Questions: Show a probable synthethic pathway to obtain the first molecule, I. Will the same strategy be used to insert the alkyl group for J. Explain. My answers (please tell me if there is any ...
sara's user avatar
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0 answers
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Friedel-Crafts's alkylation of Toluene [duplicate]

In the Friedel-Craft's alkylation of Toluene with $\ce{CH3Cl}$ in the presence of $\ce{AlCl3}$, the major product was meta - substituted. My teacher gave it to me as an exception. Is there any ...
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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 ...
Shreyansh Pachauri's user avatar
2 votes
1 answer
179 views

Order of activating ability in electrophilic aromatic substitutions

From A Guidebook to mechanism in organic chemistry by P. Sykes [1, p. 155]: The activating effect of $\ce{Y}$ on the nucleus is found to increase, i.e. the overall rate of substitution increases, in ...
SoullessWarrior's user avatar
3 votes
1 answer
111 views

Does the first step in electrophilic aromatic substitution follow equilibrium? If so, can equilibrium constant be calculated?

Using chlorine (a Lewis base) and ferric chloride (a Lewis base) as an example, the first step I saw in the textbook looks like this: The picture above depicts the Step 1 in the EAS mechanism using ...
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1 vote
1 answer
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Electrophilic attack of X+ on double bond

Is it the double bond attacking the $\ce{X+}$ ion or the other way around? Also, does it form a cyclic transition state if it isn't bromine or chlorine? Eg. cyclohexene $+ \,\ce{Cl+ ->}$ cyclic ...
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