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Chemical Properties of Ethers

An organic co...

Question

An organic compound A of molecular formula $C_{7} H_{8}$ reacts with $C l_{2}$ and NaOH to give an aromatic alcohol B of molecular formula $C_{7} H_{8} O$ which liberates $H_{2}$ With metallic sodium. Compound B on reaction with $C H_{3} C O O H$ in the presence of conc. $H_{2} S O_{4}$ forms compound C of molecular formula $C_{9} H_{10} O_{2}$ which has the fragrance of jasmine. Identify A; B. and C.
Explain the reactions.

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Solution

$A \to T o l u e n e (C_{6} H_{5} C H_{3})$
$B \to B e n z y l a l c h o l (C_{6} H_{5} C H_{2} O H_{2})$
$C \to B e n z y l a c e t a t e (C_{6} H_{5} C H_{2} O C O C H_{3})$
Reactions:
$C_{6} H_{5} C H_{3} T o l u e n e (A) C l_{2} - -- \to - H C l C_{6} H_{5} C l B e n n z y l c h l o r i d e N a O H \to C_{6} H_{5} C H_{2} O H + N a C l B e n z y l a l c h o l (B)$
$C_{6} H_{5} C H_{2} O H + H O C O C H_{3} H^{+} - --- \to - H_{2} O C_{6} H_{5} C H_{2} O C O C H_{3} B e n z y l a c e t a t e (C)$

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