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Hydroboration

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by

Kimberly Hughes

on 14 August 2013

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Transcript of Hydroboration

Hydroboration
Hydration of Alkenes by Hydroboration-Oxidation
Preparation of 1-Octanol from 1-Octene
By: Kim Hughes, Shree Thaker, and Martin Simmons
Objective
To create 1-octanol from 1-octene using Hydroboration-Oxidation. Boiling point, IR, proton NMR, and GC will be used to analyze the product.
Introduction
Hydroboration-Oxidation is a two-step process that uses BH , NaOH, and H O .
1-octene is reacted to make 1-octanol.
The reaction uses syn addition and is anti-Markovnikov
BH adds to the least substituted carbon on the double bond and 1-octene in the first step of the reaction.
Background
Herbert C. Brown discovered Hydroboration in the late 1950s.
He was born in London and eventually married Sarah Baylen who inspired him to work with Boron.
He won a Chemistry Nobel Prize for his work in 1979.
Introduction
The Electrophile in step one is the BH and the Nucleophile is 1-octene.
The Electrophile in step two is the boron complex and the -OH is the Nucleophile.
The final product is 1-octanol with the byproduct B(OH) .
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Background
Boron was discovered by Sir Humphrey Davy and Joseph-Louis Gay-Lussac. It is the most important part of the Hydroboration step.
Another important material is 1-octene.
Background
1-Octene can be an irritant and it can be ignited under almost any temperature condition.
It is stable and has low toxicity.
There are many different isomers of octene and this experiment uses the simplest form which is 1-octene where the double bond is on the 1st carbon.
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Background
The product of the reaction is 1-octanol.
It is used in perfumes, cosmetics, antifoaming agents, and food flavoring.
Used in many everyday items because it can be easily degraded in soil and water.
Background
Hydroboration-Oxidation is a two-step process
Step one has an R group replacing boron's hydrogen.
This happens three times to create a trialkylborane. The product at this point is also known as an Organoborane.
Background
Step two is the process of the hydrogen peroxide ion, after being deprotonated, attacking the product from step 1.
This happens three times and the main product is 1-octanol.
Overall Reaction
Procedure & Observation
Procedure & Observation
Results & Discussion
Results & Discussion
Results & Discussion
Conclusion
Conclusion
1. BH , THF
0 °C, 5 min
25 °C, 45 min

2. H O , NaOH (cat.)
50 °C, 1 hr
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Full transcript