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

Bihar BoardEnglish MediumSTD 12 ScienceChemistryAlcohols, Phenols, and Ethers2 Marks
Question
A compound ‘A’ having molecular formula C4H10O 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. H2SO4, 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 C4H10O is diethyl ether. Thus compound 'A' is diethylether, CH3-CH2-O-CH2-CH3.

$\text{CH}_3\text{CH}_2-\text{O}-\text{CH}_2\text{CH}_3\xrightarrow{\text{conc.}\text{H}_2\text{SO}_4}\big[\text{CH}_3-\text{CH}_2-​​\stackrel{{+}}{\hbox{O}}-\text{CH}_2-\stackrel{{. \ .}}{\hbox{O}}-\text{CH}_3\big]\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{A} \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{|}\\ \ \ \ \ \ \ \ \ \ \ \text{Diethyl ether} \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{H}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Soluble oxonium salt}$

$\text{CH}_3\text{ CH}_2\text{ OCH}_2\text{ CH}_3\xrightarrow{ \ \ \ \ \ \ \text{m} \ \ \ \ \ \ \ }2\text{CH}_3\text{ CH}_2-\text{I}\\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{A} \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \Delta \ \ \ \ \ \ \ \ \ \text{Ethyl iodide}\\ \ \ \ \ \ \ \ \ \ \ \ \ \text{Diethyl ether}$

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