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 deuterium

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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 deuterium atom add across the double bond in a syn-fashion. Since the methyl group is at the $C_1$ position,the boron atom adds to the less hindered $C_2$ position,and the deuterium atom adds to the $C_1$ position. Because it is a syn-addition,both the deuterium and the boron atom add from the same face of the cyclopentene ring. Subsequent oxidation with alkaline $H_2O_2$ replaces the boron group with a hydroxyl $(-OH)$ group with retention of configuration. Therefore,the $-OH$ group and the deuterium atom will be on the same side (cis) of the ring,and the $-OH$ group will be at the $C_2$ position while the deuterium is at the $C_1$ position. Looking at the options,the structure where $-OH$ and $D$ are cis to each other 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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