An organic compound 'A ’ having molecular formula C_3H_6 on treatment with aqueous H_2SO4 gives 'B ’ which on treatment with HCl/ ZnCl_2 gives 'C ’. The compound C on treatment with ethanolic KOH gives back the compound 'A ’. Identify the compounds A, B, C.

A=CH_3-CH=CH_2 Propene B=CH_3-CH-CH_3 | OH Propan-2-ol Cl | =CH_3-CH-CH_3 2-chloropropane CH_3-CH=CH_2 aq.H_2SO_4 CH_3-CH-CH_3 HCl/ZnCl_2 Propene (Hydration) | A OH Propan-2-ol B CH_3-CH-CH_3 Ethanolic KOH CH_3-CH=CH_2 | Propene Cl 2-Chlorophane C

An organic compound 'A ’ having molecular formula C_3H_6 on treat…

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Question

An organic compound $'A\ ’$ having molecular formula $\ce{C_3H_6}$ on treatment with aqueous $\ce{H_2SO4}$ gives $'B\ ’$ which on treatment with $\ce{HCl/ ZnCl_2}$ gives $'C\ ’.$ The compound $C$ on treatment with ethanolic $\ce{KOH}$ gives back the compound $'A\ ’.$ Identify the compounds $A, B, C.$

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Answer

$\text{A}=\text{CH}_3-\text{CH}=\text{CH}_2\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Propene}$
$\text{B}=\text{CH}_3-\text{CH}-\text{CH}_3\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{|}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{OH}\\ \ \ \ \ \ \ \ \ \ \ \ \ \text{Propan-2-ol}$
$ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Cl}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{|}\\\text{C}=\text{CH}_3-\text{CH}-\text{CH}_3\\ \ \ \ \ \ \ \ \ \ \ 2-\text{chloropropane}$
$\text{CH}_3-\text{CH}=\text{CH}_2\xrightarrow{ \ \ \ \ \ \ \text{aq}.\text{H}_2\text{SO}_4 \ \ \ \ \ }\text{CH}_3-\text{CH}-\text{CH}_3\xrightarrow{\text{HCl}/\text{ZnCl}_2}\\ \ \ \ \ \ \ \ \ \ \text{Propene} \ \ \ \ \ \ \ \ \ (\text{Hydration}) \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{|}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{A} \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{OH}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Propan-2-ol}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{B}$
$\text{CH}_3-\text{CH}-\text{CH}_3\xrightarrow{\text{Ethanolic KOH}}\text{CH}_3-\text{CH}=\text{CH}_2\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{|} \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Propene}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Cl}\\2-\text{Chlorophane}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{C}$