Methyl vinyl ether,H_2C=CH-OCH_3,reacts with | vedclass

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Question

(A) The reaction of methyl vinyl ether $(H_2C=CH-OCH_3)$ with $Br_2$ in the presence of methanol $(CH_3OH)$ follows the mechanism of electrophilic add

Vedclass · Accepted Answer

$BrCH_2-CH(OCH_3)_2$

Vedclass · Answer

(A) The reaction of methyl vinyl ether $(H_2C=CH-OCH_3)$ with $Br_2$ in the presence of methanol $(CH_3OH)$ follows the mechanism of electrophilic addition.$1$. First,the electrophile $Br^+$ attacks the double bond to form a cyclic bromonium ion intermediate.$2$. Due to the strong electron-donating $+M$ effect of the $-OCH_3$ group,the positive charge in the intermediate is highly stabilized at the carbon atom attached to the oxygen.$3$. Methanol $(CH_3OH)$ acts as a nucleophile and attacks this more substituted,positively charged carbon atom.$4$. The final product formed is $BrCH_2-CH(OCH_3)_2$.

Methyl vinyl ether,$H_2C=CH-OCH_3$,reacts with $Br_2/CH_3OH$. If methanol is reacting as water would,and if this reaction follows a typical mechanism of electrophilic addition,what would be the expected product?

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