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Hydroboration-Oxidation
Concepts tested here
- Anti-Markovnikov hydration
All Questions
2000 AIPMT 1 question
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Which reagent converts propene to 1-propanol :Acid-catalysed hydration and oxymercuration-demercuration follow Markovnikov's rule and give propan-2-ol.
Hydroboration-oxidation gives anti-Markovnikov addition of water: boron adds to the less substituted carbon, and is then replaced by –OH.
$3CH_3CH=CH_2 + \dfrac{1}{2}B_2H_6 \rightarrow (CH_3CH_2CH_2)_3B \xrightarrow{H_2O_2,\ OH^-} 3CH_3CH_2CH_2OH$
So propene is converted to 1-propanol by $B_2H_6$, $H_2O_2$ and $OH^-$.