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Question

In the reaction
(CH3)3C−O−CH2CH3+HI(1mole)heat−−−−−−−−−−→
the product(s) formed is(are):

A
(CH3)3COH and CH3CH2I
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B
(CH3)3CI and CH3CH2OH
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C
(CH3)3CI and CH3CH2I
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D
(CH3)3CO+CH2CH3I|H
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Solution

The correct option is B (CH3)3CI and CH3CH2OH
The products formed is are (CH3)3CI (tert butyl iodide) and CH3CH2OH (ethanol).

Thus we get tertiary alkyl iodide and primary alcohol. Above reaction is an example of addition of a molecule of HI to an unsymmetrical ether. The primary alcohol is formed as the tertiary carbocation is more stable. It then reacts with the iodide ion to give the product.

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