Aniline does not undergo coupling with benzene diazonium chloride at \(\mathrm{pH}<5\) because (a) Diazonium salts are less stable at low pH. (b) Coupling takes place in neutral solution. (c) The azo dye formed is soluble in acid solution. (d) Aniline is converted into \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{N}^{+} \mathrm{H}_{3} \mathrm{Cl}^{-}\) which cannot undergo coupling.

Short Answer

Expert verified
Answer: Aniline does not undergo coupling with benzene diazonium chloride at a pH lower than 5 because it is converted into \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{N}^{+}\mathrm{H}_{3}\mathrm{Cl}^{-}\), which cannot undergo coupling. In acidic conditions (pH < 5), aniline is protonated, and the resulting salt is unable to act as a nucleophile to undergo the coupling reaction with benzene diazonium chloride.

Step by step solution

01

Understand Aniline and Diazonium salts

Aniline is an aromatic amine with the formula \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\). Diazonium salts, such as benzene diazonium chloride, have the general formula \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{N}_{2} \mathrm{Cl}\). These salts can react with nucleophiles, such as aniline, to form coupling products, such as azo dyes.
02

Analyze the given options

Now, let's analyze each option and identify the correct answer: (a) Diazonium salts are less stable at low pH: Diazonium salts are generally less stable in acidic conditions, but they can still undergo coupling reactions. Therefore, this option is not the primary reason for aniline not coupling with benzene diazonium chloride at a low pH. (b) Coupling takes place in neutral solution: Coupling reactions generally occur at a neutral or slightly alkaline pH. Although this might be a factor, it does not explain why aniline is unable to undergo coupling at a pH less than 5 specifically. (c) The azo dye formed is soluble in acid solution: The solubility of the azo dye in acidic solutions is not directly related to the coupling reaction between aniline and benzene diazonium chloride. Hence, this is not the correct answer.
03

Verify the correct option

(d) Aniline is converted into \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{N}^{+}\mathrm{H}_{3}\mathrm{Cl}^{-}\) which cannot undergo coupling: In acidic conditions (pH < 5), aniline is protonated and forms a salt: $$\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2} + \mathrm{H}^{+} \rightarrow \mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{N}^{+}\mathrm{H}_{3}\mathrm{Cl}^{-}$$ This salt cannot act as a nucleophile to attack the benzene diazonium chloride. As a result, the coupling reaction does not occur at a pH less than 5. This is the correct answer.
04

Conclusion

The correct option is (d): Aniline is converted into \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{N}^{+}\mathrm{H}_{3}\mathrm{Cl}^{-}\) which cannot undergo coupling. This is because in acidic conditions (pH < 5), aniline is protonated, and the resulting salt is unable to act as a nucleophile to undergo the coupling reaction with benzene diazonium chloride.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Explain the principles of surveying.

Define surveying. Explain its importance for civil engineers.

What are the advantages and disadvantages of chain surveying?

Directions: This section contains 3 paragraphs. Based upon the paragraph, 3 multiple choice questions have to be answered. Each question has 4 choices (a), (b), (c) and (d), out of which ONLY ONE is correct. Passage I Amines have the formula \(\mathrm{RNH}_{2}\) and can be prepared by different methods. Some of them are (i) reduction of nitriles (ii) reduction of amides (iii) reduction of azides and (iv) Gabriel phthalimide synthesis. The most important property of amines is their basicity due to the presence of lone pair of electrons on nitrogen. Answer the following questions. The method, \(\mathrm{RX} \stackrel{\mathrm{KCN}}{\longrightarrow} \mathrm{RCN}, \frac{\text { (i) LiAlH }_{4} \text { lether }}{\text { (ii) } \mathrm{H}_{2} \mathrm{O}} \mathrm{RCH}_{2} \mathrm{NH}_{2}\) is not suitable for the preparation of benzyl amine because (a) \(\mathrm{RX} \stackrel{\mathrm{KCN}}{\longrightarrow} \mathrm{RCN}\) reaction is not possible since chlorobenzene does not undergo \(\mathrm{S}_{\mathrm{N}} 1\) or \(\mathrm{S}_{\mathrm{N}} 2\) reaction. (b) It is difficult to reduce \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CN}\) to \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (c) Bromobenzene gets oxidized (d) LiAlH \(_{4}\) cannot reduce \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CN}\).

What are the products obtained by the oxidation of aniline with (i) chromic acid and (ii) alkaline \(\mathrm{KMnO}_{4} ?\)

See all solutions

Recommended explanations on Chemistry Textbooks

View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free