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Aldehydes, Ketones, and Carboxylic Acids — Chemistry STD 12 Science — Question

Gujarat BoardEnglish MediumSTD 12 ScienceChemistryAldehydes, Ketones, and Carboxylic Acids3 Marks
Question
An organic compound A has the molecular formula $C_8H_{16}O_8$​​​​​​​. It gets hydrolysed with dilute sulphuric acid and gives a carboxylic acid B and an alcohol C. Oxidation of C with chromic acid also produced B. C on dehydration reaction gives but-1-ene. Write equations for the reactions involved.
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Answer

$\mathrm{A}=\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{COOCH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_3 \text { (Butyl butanoate). }$
$\mathrm{B}=\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{COOH} \text { (Butanoic acid). }$
$\mathrm{C}=\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{OH} \text { (Butan -1- ol). }$
$\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{COOCH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_3 \xrightarrow{\mathrm{H}_2 \mathrm{O} / \mathrm{H}^{+}} \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{COOH}+\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{OH} .$
$\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{OH} \xrightarrow{\mathrm{CrO}_2} \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{COOH} .$
$\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{OH} \xrightarrow{\mathrm{H}_2 \mathrm{SO}_4} \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}=\mathrm{CH}_2 \text {. }$

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