Give the major product formed by heating CH_3 | vedclass

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Question

(D) The reaction of an ether with $HI$ proceeds via an $S_N1$ or $S_N2$ mechanism depending on the nature of the alkyl groups attached to the oxygen a

Vedclass · Accepted Answer

$CH_3-CH_2-CH_2-OH + CH_3-CH_2-C(CH_3)_2-I$

Vedclass · Answer

(D) The reaction of an ether with $HI$ proceeds via an $S_N1$ or $S_N2$ mechanism depending on the nature of the alkyl groups attached to the oxygen atom.In the given ether,$CH_3-CH_2-CH_2-O-C(CH_3)_2-CH_2-CH_3$,one alkyl group is a primary alkyl group ($n$-propyl) and the other is a tertiary alkyl group ($3$-methylpentan$-3-$yl group).When an ether has a tertiary alkyl group,the reaction follows the $S_N1$ mechanism because the tertiary carbocation is highly stable.The oxygen atom is protonated by $HI$ to form an oxonium ion,which then undergoes cleavage to form the most stable carbocation.The tertiary carbocation,$CH_3-CH_2-C^+(CH_3)_2$,is formed,which then reacts with the iodide ion $(I^-)$ to form the tertiary alkyl iodide,$CH_3-CH_2-C(I)(CH_3)_2$.The remaining part forms the primary alcohol,$CH_3-CH_2-CH_2-OH$.Therefore,the major products are $CH_3-CH_2-CH_2-OH$ and $CH_3-CH_2-C(I)(CH_3)_2$.

Give the major product formed by heating $CH_3-CH_2-CH_2-O-C(CH_3)_2-CH_2-CH_3$ with $HI$.

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