- ✓Neohexyl chloride
- BSecondary butyl iodide
- CTertiary butyl bromide
- DIso-propyl iodide
e.g., $C{H_3} - O - {C_2}{H_5}\, + \,HI\,\xrightarrow{{373\,\,K}}C{H_3}I\, + \,{C_2}{H_5}OH$
The alkyl halide is formed from the smaller alkyl group.
However, in case of tertiary alkyl ether following reaction occurs.
$\mathop {C{H_3} - OC{{(C{H_3})}_3}}\limits_{ter - butyl\,\,methyl\,\,ether} + \,HI\,\xrightarrow{{373\,\,K}}$ ${(C{H_3})_3}C - I\, + \,C{H_3}OH$
The alkyl halide is formed from the tertiary alkyl group and the cleavage of such ethers occurs by $S_{N^1}$ mechanism as the product is controlled by the formation of more stable intermediate tertiary carbocation from orotonated ether.
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(nearest integer)
[Given : Molar mass of $\mathrm{AB}_2=200 \mathrm{~g} \mathrm{~mol}^{-1} \cdot \mathrm{K}_{\mathrm{b}}$
(molal boiling point elevation const. of water)
$=0.52 \mathrm{~K} \mathrm{~kg} \mathrm{~mol}^{-1}$, boiling point of water $=100^{\circ} \mathrm{C}$;
$\mathrm{AB}_2$ ionises as $\left.\mathrm{AB}_2 \rightarrow \mathrm{A}^{2+}+2 \mathrm{~B}^{-}\right]$