CH_3-C(CH_3)_2-OCH_3 xrightarrow{text{Conc. } | vedclass

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Question

(A) The reaction of ethers with concentrated $HI$ follows the $S_{N}1$ mechanism when one of the alkyl groups is tertiary,such as the tert-butyl group

Vedclass · Accepted Answer

$S_{N}1$

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(A) The reaction of ethers with concentrated $HI$ follows the $S_{N}1$ mechanism when one of the alkyl groups is tertiary,such as the tert-butyl group in this case. This is because the cleavage of the $C-O$ bond leads to the formation of a highly stable tertiary carbocation. The reaction proceeds as follows: $CH_3-C(CH_3)_2-OCH_3 + H^{+} \rightarrow CH_3-C(CH_3)_2-O^{+}(H)-CH_3$ $CH_3-C(CH_3)_2-O^{+}(H)-CH_3 \rightarrow (CH_3)_3C^{+} + CH_3OH$ Finally,the nucleophilic attack occurs: $(CH_3)_3C^{+} + I^{-} \rightarrow (CH_3)_3C-I$.

$CH_3-C(CH_3)_2-OCH_3 \xrightarrow{\text{Conc. } HI}$ The type of reaction in the above reaction is:

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