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Hydroboration
21
Transcript
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.
- 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
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
- 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.
3
- 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) .
- 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.
3
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.
Introduction
3
2
Overall Reaction
- 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.
Conclusion
3
Hydration of Alkenes by Hydroboration-Oxidation
3
1. BH , THF
0 °C, 5 min
25 °C, 45 min
2. H O , NaOH (cat.)
50 °C, 1 hr
2
Conclusion
Preparation of 1-Octanol from 1-Octene
By: Kim Hughes, Shree Thaker, and Martin Simmons
Procedure & Observation
Results & Discussion
Objective
Hydroboration
To create 1-octanol from 1-octene using Hydroboration-Oxidation. Boiling point, IR, proton NMR, and GC will be used to analyze the product.
Results & Discussion
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