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Treatment of primary amines with nitrous...

Treatment of primary amines with nitrous acid gives diazonium ions. Aliphatic diazonium ions decompose under the diazotization conditions to give complex mixture of products. Aryldiazonium ions are stable and is a valubale intermediate. They react with activated aromatic compounds to give coupling product.
At what pH phenol reacts with benzene diazonium chloride to give coupling product?

A

pH=2

B

pH=7

C

pH=9

D

pH=14

Text Solution

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The correct Answer is:
To solve the question regarding the pH at which phenol reacts with benzene diazonium chloride to give a coupling product, we can follow these steps: ### Step 1: Understand the Reaction Phenol (C6H5OH) can react with benzene diazonium chloride (C6H5N2Cl) to form a coupling product. This reaction typically occurs at the para position of the phenol ring, where the diazonium ion can substitute for a hydrogen atom. ### Step 2: Identify the Conditions for Reaction The reaction between phenol and benzene diazonium chloride requires a specific pH condition. The phenol must be in a slightly basic environment for the reaction to proceed effectively. ### Step 3: Analyze the pH Options The options provided are: - A) pH 2 (acidic) - B) pH 7 (neutral) - C) pH 9 (weakly basic) - D) pH 14 (strongly basic) ### Step 4: Determine the Suitable pH - At **pH 2**, the environment is acidic, which is not conducive for the coupling reaction. - At **pH 7**, the environment is neutral, which may not favor the reaction either. - At **pH 9**, the environment is weakly basic, which is suitable for the reaction to occur as it allows for the removal of HCl and facilitates the coupling. - At **pH 14**, the environment is strongly basic, which could lead to side reactions or degradation of the diazonium ion. ### Step 5: Conclusion The most suitable pH for the reaction of phenol with benzene diazonium chloride to yield the coupling product is **pH 9**. Therefore, the correct answer is option C. ### Final Answer **C) pH 9** ---
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At what pH phenol reacts with benzene diazonium chIoride to give coupling product?

Treatment of primary amines with nitrous acid gives diazonium ions. Aliphatic diazonium ions decompose under the diazotization conditions to give complex mixture of products. Aryldiazonium ions are stable and is a valubale intermediate. They react with activated aromatic compounds to give coupling product. What would be the product of the given reaction?

Diazonium salt formation and coupling reaction: When a reaction mixture of phenyl amine and nitrous acid is kept below 10^(@)C , a diazonium salt is formed. This reaction is called diazotization reaction. The diazonium ion, -N_(2)^(+) , is rather unstable and decomposes readily to nitrogen. However, delocalization of the diazonium from pi- bond electron over a benzene ring phenyl diazonium sufficiently for it to form at low temperature. The phenyl diazonium ion behaves as an electrophile, and will attack another arene molecule such as phenol. Electrophilic subsitiution takes at the 4 position, producing 4-hydroxy phenyl azobenzene. The reaction is known as coupling reaction. The compound formed is an energetically stable, yellow azo dye (the azo group is -N=N- ) The stability is due to extensive delocalisation of electrons via the nitrogen- nitrogen double bonds. The product which is a red azodye obtained on reacting benzene diazonium chloride with one of the following compounds :

Diazonium salt formation and coupling reaction: When a reaction mixture of phenyl amine and nitrous acid is kept below 10^(@)C , a diazonium salt is formed. This reaction is called diazotization reaction. The diazonium ion, -N_(2)^(+) , is rather unstable and decomposes readily to nitrogen. However, delocalization of the diazonium from pi- bond electron over a benzene ring phenyl diazonium sufficiently for it to form at low temperature. The phenyl diazonium ion behaves as an electrophile, and will attack another arene molecule such as phenol. Electrophilic subsitiution takes at the 4 position, producing 4-hydroxy phenyl azobenzene. The reaction is known as coupling reaction. The compound formed is an energetically stable, yellow azo dye (the azo group is -N=N- ) The stability is due to extensive delocalisation of electrons via the nitrogen- nitrogen double bonds. The azo dye obtained on reacting 4-aminophenol with nitrous acid (in dilute hydrochloric acid) below 10^(@)C and coupling the resulting diazonium salt with phenol is :

Diazonium salt formation and coupling reaction: When a reaction mixture of phenyl amine and nitrous acid is kept below 10^(@)C , a diazonium salt is formed. This reaction is called diazotization reaction. The diazonium ion, -N_(2)^(+) , is rather unstable and decomposes readily to nitrogen. However, delocalization of the diazonium from pi- bond electron over a benzene ring phenyl diazonium sufficiently for it to form at low temperature. The phenyl diazonium ion behaves as an electrophile, and will attack another arene molecule such as phenol. Electrophilic subsitiution takes at the 4 position, producing 4-hydroxy phenyl azobenzene. The reaction is known as coupling reaction. The compound formed is an energetically stable, yellow azo dye (the azo group is -N=N- ) The stability is due to extensive delocalisation of electrons via the nitrogen- nitrogen double bonds. Benzene diazonium chloride on reaction with phenol in weakly basic medium gives :

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Arenediazonium ion are weak electrophiles, they react with highly reactive aromatic compounds with phenols and tertiary aryl amines to yeild azo compounds. This electrophilic substitution is often called a diazo coupling reaction. What is the major product of given reaction?