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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.

Exceptions to the Octet Rule

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Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories:

Atomic Mass

Atomic Mass

Atoms — and the protons, neutrons, and electrons that compose them — are extremely small. For example, a carbon atom weighs less than 2 × 10−23 g. When describing the properties of tiny objects such as atoms, we use appropriately small units of measure, such as the atomic mass unit (amu). The amu was originally defined based on hydrogen, the lightest element, then later in terms of oxygen. Since 1961, it has been defined with regard to the most abundant isotope of carbon, atoms of which...

Lewis Acids and Bases

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This lesson delves into Lewis acids and bases in the context of the octet rule for electron-deficient compounds. Here, the concept is discussed, emphasizing the group 13 elements like boron or aluminium. Since group 13 elements possess three valence electrons, they form trivalent compounds with a sextet of electrons and a vacant orbital for the central atom. Consequently, these electron-deficient compounds accept electrons from other species to complete their octet in a chemical reaction. They...

Lewis Acids and Bases

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In 1923, G. N. Lewis proposed a generalized definition of acid-base behavior in which acids and bases are identified by their ability to accept or to donate a pair of electrons and form a coordinate covalent bond.
A coordinate covalent bond (or dative bond) occurs when one of the atoms in the bond provides both bonding electrons. For example, a coordinate covalent bond occurs when a water molecule combines with a hydrogen ion to form a hydronium ion. A coordinate covalent bond also results when...

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

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Related Experiment Video

Updated: Mar 27, 2026

Negative Additive Manufacturing of Complex Shaped Boron Carbides

Negative Additive Manufacturing of Complex Shaped Boron Carbides

Published on: September 18, 2018

Nothing Boring About Boron.

Lara Pizzorno¹

¹is a senior medical editor at Integrative Medicine Advisors, LLC, in Seattle, Washington.

Integrative Medicine (Encinitas, Calif.)

|January 16, 2016

Summary

This summary is machine-generated.

Boron is an essential trace mineral vital for bone health, wound healing, and hormone balance. Supplementation of 3 mg/d may benefit those with diets low in fruits and vegetables or at risk for certain conditions.

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Area of Science:

Nutritional Science
Biochemistry
Human Health

Background:

Boron is a trace mineral crucial for various metabolic processes in plants, animals, and humans.
Emerging research suggests boron's potential role in the evolution of life.
Its essentiality is underscored by its involvement in numerous physiological functions.

Purpose of the Study:

To review the diverse health benefits of the trace mineral boron.
To highlight boron's role in bone health, wound healing, and hormone regulation.
To assess the evidence for boron's therapeutic potential in chronic diseases and its safety profile.

Main Methods:

Literature review of studies on boron's physiological effects.
Analysis of research data on boron's impact on bone metabolism, inflammation, oxidative stress, and cognitive function.
Examination of studies related to boron's role in cancer prevention and treatment.

Main Results:

Boron is essential for bone growth and maintenance, wound healing, and optimizes the body's use of estrogen, testosterone, and vitamin D.
It enhances magnesium absorption, reduces inflammatory biomarkers (hs-CRP, TNF-α), and increases antioxidant enzyme levels (SOD, catalase).
Boron demonstrates protective effects against pesticide-induced oxidative stress and heavy-metal toxicity, improves cognitive function in elders, and shows preventive/therapeutic effects in various cancers.

Conclusions:

Boron plays a critical role in human health, impacting bone density, inflammation, oxidative stress, and cognitive function.
Beneficial effects are observed at intakes up to 3 mg/d, with no established harm at this level.
Consideration of 3 mg/d boron supplementation is supported for individuals with suboptimal diets or at risk for osteopenia, osteoporosis, osteoarthritis, or certain cancers.