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Acidity of Alcohols and Phenols

a An organic ...

Question

a) An organic compound (A) of molecular formula $C_{2} H_{6} O$ liberates hydrogen with metallic sodium. Compound (A) on heating with conc. $H_{2} S O_{4}$ at 440K gives an alkene (B). Compound (B) when oxidised by baeyer's reagent gives compound (C) of molecular formula $C_{2} H_{6} O_{2}$ . Identify A,B and C and explain the above reactions.
b) The metal (A) is extracted from its sulphide ore. On treatment with dilute nitric acid metal (A) gives a compound (B), which is also known as lunar caustic. (B) on heating at 723K gives (C) and $O_{2}$ . Identify A,B and C and explain the reactions.

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Solution

a)
$C_{2} H_{6} O N a \to$ liberates $H_{2}$ gas
(A) $440 K - ------ \to C o n c H_{2} S O_{4}$ $(B)$ $B a e y e r s - ---- \to R e a g e n t$ $(C)$
i) An organic compound (A) liberates $H_{2}$ gas with metallic $N a$ and so it must be a primary alcohol from the molecular formula (A) is identified as $C_{2} H_{5} O H$ ethanol $2 C_{2} H_{5} O H + 2 N a \to 2 C_{2} H_{5} O H + H_{2}$
ii) Ethanol on treatment with Conc. $H_{2} S O_{4}$ at 440K gives ethylene $C_{2} H_{4}$ as (B) $C_{2} H_{5} O H C o n c . - --- \to H_{2} S O_{4} C H_{2} = C H_{2} + H_{2} O$
iii) Ethylene on treatment with Baeyer's reagent ( Cold Dilute Alkaline $K M N O_{4}$ ) gives ethylene glycol as (C)
(b)
i) Metal (A) is silver. Silver is extracted from sulphide ore argentite $A g_{2} S$ .
ii) (A) Silver reacts with dilute nitric acid to give (B) silver nitrate which is called as lunar caustic.
$3 A g + 4 H N O_{3} \to 3 A g N O_{3} + N O + 2 H_{2} O$
iii) Lunar caustic on heating at 723K gives (C) silver nitrite $+ O_{2}$
$2 A g N O_{3} 723 K \to 2 A g N O_{2} + O_{2}$

A is Silver $A g$
B is Silver nitrate $A g N O_{3}$
C is Silver nitrite $A g N O_{2}$

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