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Question

An ether [A], C5H12O, When heated with excess of hot concentrated HI produced two alkyl halides which when reacting with aqueous NaOH yield compounds [B] and [C]. Oxidation of [B] and [C] gave a propanone and an ethanoic acid respectively. The IUPAC name of the ether [A] is :

A
2-Ethoxypropane
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B
Ethoxypropane
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C
Methoxybutane
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D
2- Methoxybutane
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Solution

The correct option is A 2-Ethoxypropane
Oxidation of primary alcohol will give carbocylic acid and oxidation of secondary alcohols will ketone.
Since, the product of oxidations are ethanoic acid and propanone, the reactant of oxidation reaction will be ethanol and 2-Propanol.
Ether (A) on reacting with excess of hot conc. HI will give alkyl iodides. These iodide are on reacting with NaOH, the OH group will replace the I group by SN2 reaction.
So, the compound (B) and (C) are Ethyl iodide and 2-Iodopropane.
Thus, the alkyl chain of (B) and (C) forms the ether compound (A).

Hence, the IUPAC name of compound (A) is 2-Ethoxypropane

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