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Alcohols, Phenols, and Ethers — Chemistry STD 12 Science — Question

Gujarat BoardEnglish MediumSTD 12 ScienceChemistryAlcohols, Phenols, and Ethers2 Marks
Question
A compound ‘A’ having molecular formula $C_4H_{10}O$ is found to be soluble in concentrated sulphuric acid. It does not react with sodium metal or potassium permanganate. On heating with excess of HI, it gives a single alkyl halide. Deduce the structure of compound A and explain all the reactions.
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Answer

  1. As compound $A$ does not react with sodium metal or potassium permanganate, it cannot be an alcohol.
  2. As compound $A$ dissolves in conc. $H_2SO_4,$ it may be an ether.
  3. As compound $A$ on heating with excess of HI gives a single alkyl halide, therefore, compound A must be a symmetrical ether.
  4. The only symmetrical ether having molecular formula $C_4H_{10}O$ is diethyl ether. Thus compound $'A'$ is diethylether, $CH_3-CH_2-O-CH_2-CH_3.$
$\text{CH}_3\text{CH}_2-\text{O}-\text{CH}_2\text{CH}_3\xrightarrow{\text{conc.}\text{H}_2\text{SO}_4}\big[\text{CH}_3-\text{CH}_2-​​\stackrel{{+}}{\hbox{O}}-\text{CH}_2-\stackrel{{. \ .}}{\hbox{O}}-\text{CH}_3\big]\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{A} \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{|}\\ \ \ \ \ \ \ \ \ \ \ \text{Diethyl ether} \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{H}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Soluble oxonium salt}$
$\text{CH}_3\text{ CH}_2\text{ OCH}_2\text{ CH}_3\xrightarrow{ \ \ \ \ \ \ \text{m} \ \ \ \ \ \ \ }2\text{CH}_3\text{ CH}_2-\text{I}\\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{A} \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \Delta \ \ \ \ \ \ \ \ \ \text{Ethyl iodide}\\ \ \ \ \ \ \ \ \ \ \ \ \ \text{Diethyl ether}$

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