MCQ
Which of the following is a primary halide?
- ✓Neohexyl chloride
- BSecondary butyl iodide
- CTertiary butyl bromide
- DIso-propyl iodide
✓
Answer
Correct option: A.
Neohexyl chloride
a
In case of unsymmetrical ethers, the site of cleavage depends on the nature of alkyl group.
In case of unsymmetrical ethers, the site of cleavage depends on the nature of alkyl group.
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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