Q26-E
Question
The alkoxymercuration of alkenes involves the formation of an organomercury intermediate (I), which is reduced with NaBH4 to give an ether product. For each reaction below, predict the ether product and provide the mechanism formation.
a.
b.
c.
Step-by-Step Solution
Verifieda.
b.
c.
The reaction is used for the formation of ether from the alkene by reacting with the water in presence of mercury acetate formation of hydromercuration product followed by sodium borohydride for demercuration and yields ether.
The reactant reacts with the \(Hg{\left( {C{H_3}C{O_2}} \right)_2}\) in presence of methanol formation of hydromercuration product occurs by breaking the double bond and addition of the \( - OC{H_3}\) to one carbon and mercuration occurs at another carbon
Then, followed by reaction with the sodium borohydride which leads to demercuration and addition of hydrogen occur and ether formed as below:
Mercuration
The reactant reacts with the \(Hg{\left( {C{H_3}C{O_2}} \right)_2}\) in presence of \({\left( {C{H_3}} \right)_2}CHOH\)product formed by mercuration that is by breaking the double bond which lead to formation of charges on carbon and addition of the \( - OCH{\left( {C{H_3}} \right)_2}\) to one carbon and mercuration occur at another carbon.
Then, followed by reaction with the sodium borohydride which leads to demercuration and addition of hydrogen occur and ether formed as below:
Mercuration-Demercuration
- Reaction occurs with the \(Hg{\left( {C{F_3}C{O_2}} \right)_2}\) in presence of ethanol. Mercuration reaction occurs by breaking the double bond which leads to the formation of small charges on carbon and addition of the \( - OC{H_2}C{H_3}\) group to one carbon and mercuration reaction occurs at another carbon.
2. Then, followed by reaction with the sodium borohydride which leads to demercuration and addition of hydrogen occur and ether formed as below:
Mercuration-demercuration