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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.

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...

Acid-Catalyzed Dehydration of Alcohols to Alkenes

Acid-Catalyzed Dehydration of Alcohols to Alkenes

In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.

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:

Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes

Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes

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...

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is activated by...

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Related Experiment Video

Updated: May 13, 2026

Spatial Profiling of Protein and RNA Expression in Tissue: An Approach to Fine-Tune Virtual Microdissection

Spatial Profiling of Protein and RNA Expression in Tissue: An Approach to Fine-Tune Virtual Microdissection

Published on: July 6, 2022

Revealing the Spatial-Molecular Fingerprint of BMP4 Expression in Breast Cancer Using ToF-SIMS and Multiple Instance

Wil Gardner¹, Judy Borg², Kellie A Mouchemore^2,3

¹Centre for Materials and Surface Science and Department of Mathematical and Physical Sciences, La Trobe University, Bundoora, Victoria 3086, Australia.

Analytical Chemistry

|February 26, 2026

Summary

We developed a new machine learning method to analyze hyperspectral imaging data from triple-negative breast cancer tumors. This approach successfully identified key spatial-molecular differences, aiding in cancer subtyping and metastasis prediction.

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A Multimodal Imaging Framework to Advance Phenotyping of Living Label-free Breast Cancer Cells

A Multimodal Imaging Framework to Advance Phenotyping of Living Label-free Breast Cancer Cells

Published on: August 22, 2025

Area of Science:

Materials Science
Biomedical Engineering
Computational Biology

Background:

Hyperspectral imaging and machine learning are advancing materials characterization.
Analyzing large hyperspectral datasets to find population-level spatial-molecular differences remains challenging.
Distinguishing similar materials, like specific cancer subtypes, requires sophisticated analytical methods.

Purpose of the Study:

To apply mass spectrometry imaging and a novel weakly supervised learning method to differentiate two similar sets of triple-negative breast cancer (TNBC).
To identify spatial-molecular signatures that distinguish TNBC tumors based on bone morphogenetic protein 4 (BMP4) expression.
To demonstrate the potential of spatial-spectral characterization for medical applications.

Main Methods:

Utilized mass spectrometry imaging (MSI) combined with a novel weakly supervised learning algorithm, stability selection-augmented multiple instance learning (SSAMIL).
SSAMIL was designed to identify generalizable, population-level spatial-molecular differences in large datasets.
Employed high-lateral resolution delayed extraction imaging for detailed spatial analysis.

Main Results:

The SSAMIL method accurately discriminated between the two TNBC sets with 92% accuracy.
Successfully identified specific spatial regions and a sparse set of molecular signatures crucial for classification.
Validated findings using expert pathology and identified a novel biomarker predictive of metastasis.

Conclusions:

The developed SSAMIL approach effectively differentiates highly similar materials, specifically TNBC subtypes.
Spatial-molecular signatures identified are critical for accurate classification and hold potential for biomarker discovery.
This study highlights the significant potential of integrated hyperspectral imaging and advanced machine learning for materials characterization and medical diagnostics.