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Chemical Properties of Ethers

Anisole is tr...

Question

Anisole is treated with HI under two different conditions.
$C + D H I (g) \leftarrow C_{6} H_{5} O C H_{3} c o n c . H I - ---- \to A + B$ The nature of A to D will be

A

A and B are $C H_{3}$ I and $C_{6} H_{5} O H,$ while C and D are $C H_{3} O H$ and $C_{6} H_{5} I$

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B

A and B are $C H_{3} O H$ and $C_{6} H_{5} I$ , while C and D are $C H_{3} I$ and $C_{6} H_{5} O H$

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C

Both A and B as well as both C and D are $C H_{3} I$ and $C_{6} H_{5} O H$

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D

A and B are $C H_{3} I$ and $C_{6} H_{5} O H$ , while there is no reaction in the second case

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Solution

The correct option is C
Both A and B as well as both C and D are $C H_{3} I$ and $C_{6} H_{5} O H$

Although in both cases products are $C H_{3} I$ and $C_{6} H_{5} O H$ ;the two reaction follow different mechanism.
$C_{6} H_{5} - O - C H_{3} H l (g) - -- \to S_{N^{2}} C H_{3} I + C_{6} H_{5} O H C_{6} H_{5} - O - C H_{3} c o n c . H l - --- \to S_{N^{1}} C H_{3} I + C_{6} H_{5} O H$
Remember that during $S_{N^{1}}$ reaction, $C H_{3}^{+}$ is formed because it is more stable than $C_{6} H_{5}^{+} .$

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A

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