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Answer in brief · Q4

Q.Give the reagents and conditions necessary to prepare phenol from
a. Chlorobenzene
b. Benzene sulfonic acid.

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Part a. From chlorobenzene (Dow process, section 11.4.2). Chlorobenzene is fused with NaOH under forcing conditions: 623 K (high temperature) and 300 atm (high pressure). This displaces the ring chlorine, forming sodium phenoxide (C6H5-O-Na). The sodium phenoxide is then treated with dilute HCl (H3O+), which protonates the phenoxide ion and liberates phenol.

Reagents/conditions: (i) NaOH, 623 K, 300 atm;

(ii) dilute HCl.

Part b. From benzene sulfonic acid (section 11.4.2). Benzene sulfonic acid (C6H5-SO3H) is first neutralised with NaOH (an ordinary acid-base reaction) to give sodium benzene sulfonate (C6H5-SO3Na). This salt is then fused with SOLID NaOH at 573 K, a more forcing alkali-fusion step that displaces the sulfonate group entirely and gives sodium phenoxide. Finally, acidifying with dilute HCl liberates phenol. …

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