CBSE 2025, Set 1

Question

An organic compound (A) (molecular formula C$_8$H$_{16}$O$_2$) was hydrolysed with dilute sulphuric acid to get a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid produced (B). (C) on dehydration gives But-1-ene. Identify (A), (B) and (C) and write chemical equations for the reactions involved.

Edvaya · Accepted Answer

The correct answer is Subjective. **Identification:** - **(C) dehydration $ightarrow$ But-1-ene:** C must be a **primary alcohol with 4 carbons** $ightarrow$ **C = Butan-1-ol (C$_4$H$_9$OH)** - **(C) oxidation with CrO$_3$ $ightarrow$ (B):** Primary alcohol oxidised to carboxylic acid $ightarrow$ **B = Butanoic acid (C$_3$H$_7$COOH)** - **(A) hydrolysis $ightarrow$ B + C:** A is an ester of butanoic acid and butan-1-ol $ightarrow$ **A = Butyl butanoate (C$_3$H$_7$COOC$_4$H$_9$)** - This molecular formula matches C$_8$H$_{16}$O$_2$. **Chemical Equations:** ![Q33B reaction scheme — butyl butanoate hydrolysis, oxidation and dehydration](https://www.edvaya.com/images/chemistry/cbse/2025/set1/q33b-butyl-butanoate-reactions.webp) $$\underbrace{	ext{C}_3	ext{H}_7	ext{COOC}_4	ext{H}_9}_{(A)} + 	ext{H}_2	ext{O} \xrightarrow{	ext{dil. H}_2	ext{SO}_4} \underbrace{	ext{C}_3	ext{H}_7	ext{COOH}}_{(B)} + \underbrace{	ext{C}_4	ext{H}_9	ext{OH}}_{(C)}$$ $$\underbrace{	ext{C}_4	ext{H}_9	ext{OH}}_{(C)} \xrightarrow{	ext{CrO}_3/	ext{CH}_3	ext{COOH}} \underbrace{	ext{C}_3	ext{H}_7	ext{COOH}}_{(B)}$$ $$\underbrace{	ext{C}_4	ext{H}_9	ext{OH}}_{(C)} \xrightarrow{	ext{Conc. H}_2	ext{SO}_4,\,\Delta} 	ext{CH}_3	ext{CH}_2	ext{CH=CH}_2 + 	ext{H}_2	ext{O}$$

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