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Chlorobenzene on fusing with solid NaOH ...

Chlorobenzene on fusing with solid NaOH follwed by acidification gives 

A

Benzene

B

Benzoic acid

C

Phenol

D

Benzene chloride

Text Solution

Verified by Experts

The correct Answer is:
C
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An organic compound (A) of molecular weight 135 on boiling with NaOH evolves a gas which gives white dense fumes on bringing a rod dipped in HCl near it. The alkaline solution thus obtained on acidification gives the precipitate of a compound (B) having molecular weight 136. Treatment of (A) with HNO_2 also yeilds (B), whereas its treatment with Br_2//KOH gives (C). compound (C) reacts with cold HNO_2 to give(D), which gives red colour with ceric ammonium nitrate. On the other hand(E) an isomer of (A) on boiling with dil HCl gives an acid (F), having molecular weight 136. On oxidation followed by heating, (F) gives an anhydride (G) which condenses with benzene in presence of AlCl_3 to give anthraquinone. IUPAC name of compound (B) is

An organic compound (A) of molecular weight 135 on boiling with NaOH evolves a gas which gives white dense fumes on bringing a rod dipped in HCl near it. The alkaline solution thus obtained on acidification gives the precipitate of a compound (B) having molecular weight 136. Treatment of (A) with HNO_2 also yeilds (B), whereas its treatment with Br_2//KOH gives (C). compound (C) reacts with cold HNO_2 to give(D), which gives red colour with ceric ammonium nitrate. On the other hand(E) an isomer of (A) on boiling with dil HCl gives an acid (F), having molecular weight 136. On oxidation followed by heating, (F) gives an anhydride (G) which condenses with benzene in presence of AlCl_3 to give anthraquinone. Structural formula of compound (C) is

An organic compound (A) of molecular weight 135 on boiling with NaOH evolves a gas which gives white dense fumes on bringing a rod dipped in HCl near it. The alkaline solution thus obtained on acidification gives the precipitate of a compound (B) having molecular weight 136. Treatment of (A) with HNO_2 also yeilds (B), whereas its treatment with Br_2//KOH gives (C). compound (C) reacts with cold HNO_2 to give(D), which gives red colour with ceric ammonium nitrate. On the other hand(E) an isomer of (A) on boiling with dil HCl gives an acid (F), having molecular weight 136. On oxidation followed by heating, (F) gives an anhydride (G) which condenses with benzene in presence of AlCl_3 to give anthraquinone. Structrual formula of compound (A) is