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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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Formation of Halohydrin from Alkenes02:41

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An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
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Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes01:33

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Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
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Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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Introduction
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Butanol formation from gaseous substrates.

Peter Dürre1

  • 1Institut für Mikrobiologie und Biotechnologie, Universität Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany peter.duerre@uni-ulm.de.

FEMS Microbiology Letters
|February 24, 2016
PubMed
Summary
This summary is machine-generated.

This study explores producing butanol from gases like carbon monoxide and carbon dioxide using acetogens and engineered cyanobacteria, offering an economical and sustainable alternative to sugar fermentation.

Keywords:
Clostridium carboxidivoransClostridium ljungdahliiautotrophic acetogensbutanolsyngas

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Area of Science:

  • Biotechnology
  • Microbiology
  • Synthetic Biology

Background:

  • Butanol is primarily produced via acetone-butanol-ethanol (ABE) fermentation by saccharolytic anaerobes.
  • Alternative butanol production from synthesis gas (carbon monoxide and hydrogen) by autotrophic acetogens is economically advantageous and avoids competition with food sources.

Purpose of the Study:

  • To investigate and highlight biotechnological routes for butanol production from gaseous substrates.
  • To present alternatives to traditional sugar-based fermentation for butanol synthesis.

Main Methods:

  • Utilizing autotrophic acetogens like Clostridium species for butanol production from synthesis gas.
  • Employing metabolic engineering strategies in bacteria (e.g., Clostridium ljungdahlii) for enhanced butanol yield.
  • Engineering cyanobacteria (Synechococcus sp. PCC 7942) for photoautotrophic butanol production from CO2.

Main Results:

  • Clostridium carboxidivorans naturally produces butanol from gaseous substrates.
  • Metabolic engineering of Clostridium ljungdahlii demonstrated successful butanol production.
  • Recombinant cyanobacteria enabled butanol synthesis from CO2 under photoautotrophic conditions.

Conclusions:

  • Butanol production from abundant gases (CO, CO2) presents a cost-effective and sustainable alternative to conventional fermentation.
  • Autotrophic acetogens and engineered cyanobacteria are promising platforms for gas-based butanol bio-production.
  • This approach mitigates substrate competition with human nutrition and offers economic benefits.