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11 votes
1 answer
2k views

Why does boron add to the less substituted carbon in the hydroboration of an alkene?

In the hydroboration of a typical alkene, the boron fragment ends up attached to the less substituted carbon: What are the electronic or steric factors that lead to this regioselectivity?
jyoti proy's user avatar
  • 1,024
2 votes
1 answer
4k views

What is the stereochemistry resulting from hydroboration of 1-methylcyclopentene?

What is the major product of the following reaction sequence? I'm supposed to work out the structures of both 2 and 3, but I already know 2 to be 1-methylcyclopentene (as the most substituted ...
john clastings's user avatar
7 votes
2 answers
3k views

Hydroboration/oxidation vs acid-catalyzed hydration of 1-phenylpropene

I am trying to predict the products of both the hydroboration/oxidation and acid-catalyzed hydration of 1-phenylpropene: Both C1 and C2 of the double bond are secondary carbons. However, I have the ...
Musicpulpite's user avatar