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Question: What stereoisomers are obtained from hydroboration-oxidation of \( 1 \) -ethyl cyclohexene?...

What stereoisomers are obtained from hydroboration-oxidation of 11 -ethyl cyclohexene?

Explanation

Solution

11 -ethyl cyclohexene is a cycloalkene in which ethyl group is substituted at the C1{C_1} carbon. Hydroboration-oxidation reaction is the addition of boron trihydride to an alkene further the addition of hydroxide replaces the BH2B{H_2} group and substitutes the hydroxyl group. Different isomers were obtained when hydroboration-oxidation of 11 -ethyl cyclohexene is done.

Complete answer:
Stereoisomers are the chemical compounds that contain the same molecular formula, but there is a difference of direction of arrangement of atoms or groups in the molecule.
11 -ethyl cyclohexene is a cycloalkene in which an ethyl group is substituted at the C1{C_1} carbon. Hydroboration is the reaction of addition of simple boranes like BH3B{H_3} to alkene, which results in the addition of HH and BH2B{H_2} units leading to the formation of alkyl boranes.
Later this alkyl boranes when treated with hydrogen peroxide which is an oxidation reaction leads to the formation of alcohols as BH2B{H_2} is replaced by hydroxide ion from hydrogen peroxide. There is no formation of intermediates as only the transition state was formed.
The hydroboration-oxidation of 11 -ethyl cyclohexene is:

Though the formed two products are with the same molecular formula, there is a difference in the arrangement of groups that leads to the formation of stereoisomers.
The product 11 is (1S,2R)2ethylcyclohexanol\left( {1S,2R} \right) - 2 - ethylcyclohexanol
The product 11 is (1R,2S)2ethylcyclohexanol\left( {1R,2S} \right) - 2 - ethylcyclohexanol .

Note:
The overall reaction favours the anti-markovnikov's rule as the hydroxide group is attached to the carbon containing more number of hydrogen atoms. The addition of borane favours the syn-addition as both HH and BH2B{H_2} units were added at the same side of the double bond.