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1 vote
1 answer
98 views

Hydroboration–oxidation reaction without THF

The first step of hydroboration–oxidation usually involves $\ce{BH3}$ accompanied by THF. Is it possible for hydroboration to occur without the presence of THF? Borane is incredibly reactive. Wouldn't ...
user28684's user avatar
1 vote
0 answers
36 views

Hydroboration, steroselectivity and anti-markovnikov product [duplicate]

My first question has to do with the fact that Hydroboration produces an anti-markovnikov product, why?. I don't see how that happens. A wikipedia artical says that B has a partial positive charge ...
bobbylee's user avatar
6 votes
2 answers
713 views

What is the mechanism for the reaction of alkenes with diborane and chloramine?

$$\ce{CH3-CH=CH2 ->[B2H6/THF][NH2Cl/H2O, Δ] Product (P)}$$ What is $\ce{Product (P)}?$ First of all, in this reaction I performed hydroboration to form an alkylborane. But I don't have any ideas ...
raj pattnaik's user avatar
4 votes
0 answers
282 views

Rationalise the Relative Reactivity of Borane and DIBAL as Reductants

In Clayden's Organic Chemistry (Second Edition) it is written that borane is useful in chemoselectively reducing the most nucleophilic carbonyl to its corresponding alcohol. It is later said that ...
Jacob's user avatar
  • 884
15 votes
1 answer
13k views

What happens when an alkylborane is treated with acetic acid?

In the hydroboration reactions of alkenes I've seen so far, they were always followed by oxidation with $\ce{H2O2/NaOH}$ (to yield alcohols). Today I found a peculiar reaction in which acetic acid-...
Ritwik Das's user avatar
  • 2,209
3 votes
1 answer
342 views

Why is an alkoxide released instead of hydroxide in the attack of trialkyloxyborane by hydroxide?

In the mechanism of a hydroboration-oxidation, the oxidation part includes a nucleophilic attack of a hydroxide on a trialkyloxyborane ( $\ce{B(OR)_3}$ where $\ce{R}$ is an alkyl group). It creates ...
phi2k's user avatar
  • 1,441