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An organic compound [A], having a specific smell forms two compounds [B] and [C] by reacting with…
(i)[3.0]
An organic compound [A], having a specific smell forms two compounds [B] and [C] by reacting with conc. sodium hydroxide. The molecular formula of compound [B] is $\text{C}_7\text{H}_8\text{O}$, which forms compound [A] again on oxidation. Compound [C] forms benzene on heating with soda lime.
Write the structures of compounds [A], [B] and [C]. Also, write the reactions involved.
(ii)[2.0]
Identify the compounds [A] and [B] in the reactions given below:
(a) $\text{C}_6\text{H}_6 \xrightarrow[\text{AlCl}_3(\text{anhy.})]{\text{CH}_3\text{Cl}} [\text{A}] \xrightarrow[\text{K}_2\text{Cr}_2\text{O}_7 + \text{H}_2\text{SO}_4]{[\text{O}]} [\text{B}]$
(b) $\text{CH}_3\text{-CHOH-CH}_3 \xrightarrow[\text{K}_2\text{Cr}_2\text{O}_7 + \text{H}_2\text{SO}_4]{[\text{O}]} [\text{A}] \xrightarrow{\text{NH}_2\text{OH}} [\text{B}]$
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From ISC 2024 Chemistry Paper 1, question 19.