Which of the following will not give the same | vedclass

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(B) Hydroboration-oxidation follows anti-Markownikoff's rule (syn-addition of $H$ and $OH$),while acid-catalysed hydration follows Markownikoff's rule

Vedclass · Accepted Answer

$1-$Methylcyclohexene

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(B) Hydroboration-oxidation follows anti-Markownikoff's rule (syn-addition of $H$ and $OH$),while acid-catalysed hydration follows Markownikoff's rule and involves a carbocation intermediate,which may undergo rearrangement.For symmetric alkenes like $CH_2=CH_2$ or $CH_3-CH=CH-CH_3$,both processes yield the same product.For cyclic alkenes like cyclohexene,the products are the same (cyclohexanol).However,for unsymmetrical alkenes like $1$-methylcyclohexene,acid-catalysed hydration leads to a more stable tertiary carbocation,resulting in $1$-methylcyclohexanol,whereas hydroboration-oxidation adds $OH$ to the less substituted carbon,resulting in $2$-methylcyclohexanol. Thus,they give different products.

Which of the following will not give the same product on hydroboration-oxidation and acid-catalysed hydration?

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