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Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

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.

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...

Preparation of Alcohols via Addition Reactions

Preparation of Alcohols via Addition Reactions

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...

Radical Substitution: Allylic Bromination

Radical Substitution: Allylic Bromination

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...

Esters to Carboxylic Acids: Saponification

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Esters can be hydrolyzed to carboxylic acids under acidic or basic conditions. Base-promoted hydrolysis of esters is a nucleophilic acyl substitution reaction in which esters react with an aqueous base, followed by an acid to give carboxylic acids. This reaction is also known as saponification because it forms the basis for making soaps from fats.
The reaction requires a base in stoichiometric amounts, which participates in the reaction and is not regenerated later. So, the base acts as a...

Oxidation of Alcohols

Oxidation of Alcohols

In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:

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Related Experiment Video

Updated: Aug 22, 2025

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

Modifying the Stöber Process: Is the Organic Solvent Indispensable?

Jinxin Wang¹, Kaimin Zhang¹, Safiyye Kavak²

¹Department of Chemistry, University of Antwerp, Universiteitsplein 1, 2610, Antwerpen, Belgium.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|November 7, 2022

Summary

Researchers found that organic solvents are not essential for the Stöber method synthesis of silica spheres. An immiscible synthesis method was developed, enabling solvent-free production of uniform silica nanoparticles.

Keywords:

Stöber process controllable particle size materials science nanoparticles organic solvent-free

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Last Updated: Aug 22, 2025

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

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Published on: October 30, 2018

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Area of Science:

Materials Science
Nanotechnology
Inorganic Chemistry

Background:

The Stöber method is a foundational technique for synthesizing inorganic nanomaterials.
A significant drawback of the Stöber method is its reliance on substantial quantities of organic solvents.

Purpose of the Study:

To investigate the possibility of omitting organic solvents in the Stöber method.
To develop an alternative synthesis route for silica particles without organic solvents.

Main Methods:

Exploration of ethanol's role in the Stöber synthesis of silica spheres.
Development of an initially immiscible synthesis method as a replacement for the organic solvent-based Stöber process.

Main Results:

Ethanol, while influencing particle size and uniformity, was found not to be indispensable.
A novel immiscible synthesis method successfully produced silica particles in the same size range as the traditional Stöber process, without organic solvents.

Conclusions:

Organic solvents can be omitted from the Stöber synthesis of silica particles.
The newly discovered immiscible synthesis method offers a greener alternative for silica nanoparticle production.
This solvent-free approach holds potential for broader applications in synthesizing other Stöber-based materials.