Question
When mixed ethers in which primary or secondary alkyl group is present is treated with one mole of HI , the iodide ion $\left( I ^{-}\right)$goes to which alkyl group and why?
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$\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Br}\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\text{CH}_3-\text{CH}-\text{CH}-\text{CH}_3\xrightarrow{\ \ \ \text{HBr} \ \ }\text{CH}_3-\text{C}-\text{CH}_2-\text{CH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ |\ \ \ \ \ \ \ \ \ \ |\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3\ \ \ \ \text{OH}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3$
Give a mechanism for this reaction.
(Hint: The secondary carbocation formed in step II rearranges to a more stable tertiary carbocation by a hydride ion shift from 3rd carbon atom.)