Aromatic amines – forming dyes

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Aromatic amines – forming dyes L.O: To be able to describe how aromatic amines react to form dyes

Benzene diazonium chloride Formula: C6H5N2+ Cl¯. A diazonium group is attached to the ring. The aromatic ring helps stabilise the ion How are they prepared? reagents Phenylamine, nitrous acid and hydrochloric acid conditions Keep BELOW 10°C equation C6H5NH2 + HNO2 + HCl C6H5N2+ Cl¯ + 2H2O N.B. Nitrous acid is unstable and is made in situ from sodium nitrite C6H5NH2 + NaNO2 + 2HCl C6H5N2+ Cl¯ + NaCl + 2H2O Keeping the solution cold slows down decomposition of the diazonium salt C6H5N2+ Cl¯ + H2O C6H5OH + HCl + N2

Diazonium salts - reactions Benzene diazonium chloride undergoes two main types of reaction SUBSTITUTION OF THE DIAZONIUM GROUP (nitrogen expelled) COUPLING REACTIONS (nitrogen atoms are retained)

Diazonium salts - substitution Substitution by OH reagents water (HYDROLYSIS) conditions warm above 10°C equation C6H5N2+ Cl¯ + H2O C6H5OH + HCl + N2 Where is this used? The only reasonably simple way to substitute OH and forms the last step in the production of phenol. Phenol is an antiseptic and is used to make polymers. Substitution by I reagents potassium iodide solution conditions warm equation C6H5N2+ Cl¯ + KI C6H5I + KCl + N2

Diazonium salts - coupling reagents phenol and sodium hydroxide conditions alkaline solution below 10°C equation C6H5N2+Cl¯ + C6H5OH + NaOH C6H5-N=N-C6H4OH + NaCl + H2O (4-hydroxyphenol)azobenzene ORANGE This type of reaction is used in making azo dyes AZO GROUP