Benzene diazonium chloride on hydrolysis gives

Chemical Reactions of Diazonium Salts -I What is a Diazonium Salt? Diazonium salts are a group of organic compounds which share a common functional group R – N 2 + X – where R denotes some organic residue (such as an alkyl or aryl group) and X is an organic or inorganic anion (a 2 + is commonly referred to as a diazonium group. For example, C 6H 5N 2 +Cl – is known as benzene-diazonium chloride. Diazonium salts are colourless crystalline solids and are readily soluble in water. They decompose easily in a dry state. Chemical Reactions of Diazonium Salts Diazonium salts undergo two types of reactions: • Reactions which involve the replacement of nitrogen • Reactions which involve retention of the diazo group. This article deals with the reactions which involve the replacement of nitrogen. Diazonium group is a good leaving group. They are substituted by other groups such as Cl –, Br –, CN –, and OH – which easily displace nitrogen from the aromatic ring. This nitrogen escapes from the reaction mixture in the form of a gas. 1. Replacement by halide or cyanide ion: The –, Br –, CN – can be easily introduced into the benzene ring in the presence of Cu (I) ion. This reaction is commonly known as the Sandmeyer reaction. 2. Replacement by iodide ion: It is not easy to introduce 3. Replacement by hydroxyl group: If the temperature of the diazonium salt solution is increased to 283 K, the salt gets hydrolyzed to phenol. 4. Replacement by –NO 2 group: When we heat diazonium fluo...

Q. An organic compound A ( C 8 H 6 ) gives brick red precipitate with ammoniacal solution of C u 2 C l 2. A on treatment with ammoniacal solution of H g S O 4 yields B ( C 8 H 8 O ), B gives positive iodoform test B can also be prepared by the reaction of benzene with acetic anhydride in presence of A l C l 3 identify A and B.

\( \newcommand\) • • • • • • • • • This page looks at some typical reactions of diazonium ions, including examples of both substitution reactions and coupling reactions. If you have come straight to this page from a search engine and want to know about the preparation of the diazonium ions. Substitution reactions of diazonium ions Diazonium ions are present in solutions such as benzenediazonium chloride solution. They contain an -N 2 + group. In the case of benzenediazonium chloride, this is attached to a benzene ring. Benzenediazonium chloride looks like this: In this set of reactions of the diazonium ion, the -N 2 + group is replaced by something else. The nitrogen is released as nitrogen gas. Substitution by an -OH group To get this reaction, all you need to do is warm the benzenediazonium chloride solution. The diazonium ion reacts with the water in the solution and phenol is formed - either in solution or as a black oily liquid (depending on how much is formed). Nitrogen gas is evolved. This is the same reaction that you get if you react phenylamine with nitrous acid in the warm. The diazonium ion is formed first and then immediately reacts with the water in the solution to give phenol. Substitution by an iodine atom This is a good example of the use of diazonium salts to substitute things into a benzene ring which are otherwise quite difficult to attach. (That's equally true of the previous reaction, by the way.) If you add potassium iodide solution to the benzenedia...

https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FMap%253A_Organic_Chemistry_(Vollhardt_and_Schore)%2F22%253A_Chemistry_of_the_Benzene_Substituents%253A_Alkylbenzenes_Phenols_and_Benzenamines%2F22.11%253A_%2509Electrophilic_Substitution_with_Arenediazonium_Salts%253A_Diazo__Coupling Expand/collapse global hierarchy • Home • Bookshelves • Organic Chemistry • Map: Organic Chemistry (Vollhardt and Schore) • 22: Chemistry of the Benzene Substituents: Alkylbenzenes, Phenols, and Benzenamines • 22.11: Electrophilic Substitution with Arenediazonium Salts: Diazo Coupling Expand/collapse global location Sulfa Drug Synthesis Sulfa drugs are an important group of synthetic antimicrobial agents (pharmaceuticals) that contain the sulfonamide group. The synthesis of sulfanilamide (a sulfa drug) illustrates how the reactivity of aniline can be modified to make possible an electrophilic aromatic substitution. The corresponding acetanilide undergoes chlorosulfonation. The resulting 4-acetamidobenzenesulfanyl chloride is treated with ammonia to replace the chlorine with an amino group and affords 4-acetamidobenzenesulfonamide. The subsequent hydrolysis of the sulfonamide produces the sulfanilamide.