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Hydroboration-Oxidation of Alkenes: Mechanism, Regio- & Stereochemistry, Efficiency, Lecture notes of Chemistry

American Conservatory Theater (A.C.T.)Chemistry

An in-depth look at the hydroboration-oxidation reaction of alkenes, focusing on the mechanism, regio- and stereochemistry, and efficiency of the process. Prepared by josé laboy, ms, the resource can be found at <http://www.chem.wisc.edu/areas/clc>. The addition of borane to the most substituted carbon atom of the double bond, the retention of configuration during oxidation, and the anti-markovnikov addition and syn-addition outcomes.

What you will learn

  • What is the regio- and stereochemistry of the hydroboration-oxidation reaction of alkenes?
  • How efficient is the hydroboration-oxidation reaction of alkenes?
  • What is the mechanism of the hydroboration-oxidation reaction of alkenes?

Typology: Lecture notes

2021/2022

Uploaded on 09/12/2022

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dylanx 🇺🇸

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Chem%343%–%Organic%Reactions%
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http://www.chem.wisc.edu/areas/clc'(Resource'page)!
Alkene%Reactions%#8:!Hydroboration-Oxidation!
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Sodium!borate!
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The!hydrogen!atom!of!borane!adds!to!the!most!substituted!carbon!atom!of!the!
double!bond!leaving!the!boron!atom!on!the!least!substituted!carbon!atom.!!
Oxidation!of!boron!occurs!with!retention!of!configuration.!
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1) BH3 / THF
2) H2O2 / NaOH OH
H
BH2BH22 more times
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HO O
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2 more times
O
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O
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HO
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OHO
H
OH
+B(OH)3
Na3BO4
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Partial preview of the text

Download Hydroboration-Oxidation of Alkenes: Mechanism, Regio- & Stereochemistry, Efficiency and more Lecture notes Chemistry in PDF only on Docsity!

Chem 343 – Organic Reactions Chapter 5 & 7 Prepared by José Laboy, MS http://www.chem.wisc.edu/areas/clc (Resource page) Alkene Reactions #8 : Hydroboration-­‐Oxidation Mechanism Sodium borate The hydrogen atom of borane adds to the most substituted carbon atom of the double bond leaving the boron atom on the least substituted carbon atom. Oxidation of boron occurs with retention of configuration.

  1. BH 3 / THF
  2. H 2 O 2 / NaOH (^) OH H BH 2 BH 2 2 more times B HO O
  • OH O B 2 more times O B O O HO 2 more times O (^) H (^) O H OH
  • B(OH) 3 Na 3 BO 4

The regiochemistry of the reaction is anti-­‐Markovnikov addition. The stereochemistry is a syn -­‐addition. (see Example below) The outcome of the reaction is an anti-­‐Markovnikov alcohol. The reaction is very efficient; one equivalent of borane can produce three equivalents of alcohol product. H 3 C

  1. BH 3 / THF
  2. H 2 O 2 / NaOH CH 3 H OH racemic