The following compound can readily be prepared by Williamson ether synthesis by reaction between:

  • A
    Bicyclo[$2.2$.$2$]octan$-1-$ol and benzyl chloride
  • B
    Bicyclo[$2.2$.$2$]octan$-1-$ol and benzyl iodide
  • C
    $1-$Chlorobicyclo[$2.2$.$2$]octane and benzyl alcohol
  • D
    $1-$Iodobicyclo[$2.2$.$2$]octane and benzyl alcohol

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Predict the major product for the following reaction:
$m-CH_3O-C_6H_4-CH_2CH_2-O-CH(CH_3)Ph \xrightarrow{HI (excess), \text{heat}} ?$

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Predict the major products for the following reaction:
$\text{Cyclohexyl-O-C(CH}_3)_3 \xrightarrow{HI \text{ (excess)}, \Delta} ?$

Explain the reaction of methoxyethane with concentrated $HI$ and describe its mechanism.

The reaction of $tert$-butyl methyl ether with one equivalent of $HI$ gives:

An ether $(A)$,$C_5H_{12}O$,when heated with excess of hot concentrated $HI$ produced two alkyl halides which when treated with $NaOH$ yielded 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

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