Hydroboration of 1-methylcyclopentene using B | vedclass

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(A) Hydroboration-oxidation is a $syn$-addition reaction. In the hydroboration of $1$-methylcyclopentene with $B_2D_6$,the boron atom and the deuteriu

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Vedclass · Answer

(A) Hydroboration-oxidation is a $syn$-addition reaction. In the hydroboration of $1$-methylcyclopentene with $B_2D_6$,the boron atom and the deuterium atom add to the same side of the double bond. Subsequently,the oxidation step with alkaline hydrogen peroxide $(H_2O_2/OH^-)$ replaces the boron atom with a hydroxyl group $(-OH)$ with retention of configuration. Since the addition is $syn$,the $-D$ and $-OH$ groups will be on the same side of the cyclopentane ring. Looking at the options,the structure where $-D$ and $-OH$ are on the same side (cis) is represented in option $A$.

Hydroboration of $1$-methylcyclopentene using $B_2D_6$,followed by treatment with alkaline hydrogen peroxide,gives

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