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Hydrocarbons question

2019 · 8 Apr · Shift 2 · Q2
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Hydrocarbons question

2019 · 8 Apr · Shift 2 · Q2

JEE MainChemistryHydrocarbonsMCQ+4 / −1
Polysubstitution is a major drawback in:
  1. A
    Reimer Tiemann reaction
  2. B
    Friedel Craft's alkylation
  3. C
    Acetylation of aniline
  4. D
    Friedel Craft's acylation
View written solutionFree

Correct answer: B

  1. Understand the question

We need to identify the reaction in which polysubstitution is a major drawback.

Polysubstitution means that after one substituent enters the aromatic ring, the product becomes even more reactive and undergoes further substitution, giving di-/tri-substituted products.


  1. Check each option

A. Reimer–Tiemann reaction

This reaction is used for formylation of phenols, typically giving salicylaldehyde.

  • It is not especially known for polysubstitution as the major drawback.
  • Main issue is usually mixture of ortho/para products or moderate yield.

So, A is not correct.


B. Friedel–Crafts alkylation

In Friedel–Crafts alkylation, an alkyl group is introduced into an aromatic ring using an alkyl halide and a Lewis acid such as AlCl3\text{AlCl}_3AlCl3​.

Example:

Benzene→AlCl3RClAlkylbenzene\text{Benzene} \xrightarrow[\text{AlCl}_3]{\text{RCl}} \text{Alkylbenzene}BenzeneRClAlCl3​​Alkylbenzene

Now, an alkyl group is electron-donating due to the +I+I+I effect and hyperconjugation. Therefore, once the first alkyl group enters the ring, the ring becomes more reactive than benzene itself.

So the product alkylbenzene undergoes further alkylation easily:

Alkylbenzene→dialkylbenzene→trialkylbenzene\text{Alkylbenzene} \to \text{dialkylbenzene} \to \text{trialkylbenzene}Alkylbenzene→dialkylbenzene→trialkylbenzene

Hence, polysubstitution is a major drawback of Friedel–Crafts alkylation.

So, B is correct.


C. Acetylation of aniline

Acetylation of aniline forms acetanilide:

C6H5NH2→CH3COCl or (CH3CO)2OC6H5NHCOCH3\text{C}_6\text{H}_5\text{NH}_2 \xrightarrow{\text{CH}_3\text{COCl or } (\text{CH}_3\text{CO})_2\text{O}} \text{C}_6\text{H}_5\text{NHCOCH}_3C6​H5​NH2​CH3​COCl or (CH3​CO)2​O​C6​H5​NHCOCH3​

This is protection of the amino group, not an aromatic substitution reaction where polysubstitution is the main issue.

So, C is not correct.


D. Friedel–Crafts acylation

In Friedel–Crafts acylation, an acyl group is introduced:

Benzene→AlCl3RCOClAryl ketone\text{Benzene} \xrightarrow[\text{AlCl}_3]{\text{RCOCl}} \text{Aryl ketone}BenzeneRCOClAlCl3​​Aryl ketone

The acyl group is electron-withdrawing due to the −I-I−I and −M-M−M effects, so after one acyl group enters, the ring becomes less reactive.

Therefore, polysubstitution does not occur easily in Friedel–Crafts acylation.

So, D is not correct.


  1. Conclusion

The reaction in which polysubstitution is a major drawback is:

B. Friedel–Craft’s alkylation\boxed{\text{B. Friedel–Craft's alkylation}}B. Friedel–Craft’s alkylation​
  1. Comparison with stored correct answer

Stored correct answer: B

Our derived answer: B

They match.

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