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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.

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the bromine molecule...

Carbocations

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...

Overview of Advanced Functional Groups

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Functional groups are groups of atoms with specific chemical properties that occur within organic molecules and are sometimes denoted as “R”. Functional groups can “functionalize” a compound by enabling it to adopt different physical and chemical properties.
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IUPAC Nomenclature of Aldehydes

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Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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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: Jun 1, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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(4-Carbamoylphen-yl)boronic acid.

Margarita D Apostolova, Rositsa P Nikolova, Boris L Shivachev

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study details the crystal structure of a novel boron-containing compound, C(7)H(8)BNO(3). The molecule exhibits statistical disorder and forms sheet-like structures through hydrogen bonding.

Area of Science:

Crystallography
Supramolecular Chemistry
Boron Chemistry

Background:

Understanding the molecular arrangement and bonding in novel chemical compounds is crucial for materials science.
Boron-containing organic molecules offer unique structural and electronic properties.
Hydrogen bonding plays a significant role in the self-assembly of crystalline structures.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(7)H(8)BNO(3).
To investigate the molecular disorder and intermolecular interactions within the crystal lattice.
To analyze the spatial arrangement of the boronic acid and amide functional groups relative to the benzene ring.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.

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Analysis of hydrogen bonding networks (N-H⋯O and O-H⋯O) to understand crystal packing.

Geometric analysis to quantify the torsion angles of the functional groups from the benzene ring plane.

Main Results:

The molecule C(7)H(8)BNO(3) crystallizes with the molecule situated on an inversion center.
Statistical disorder was observed between the boronic acid [B(OH)(2)] and amide [CONH(2)] groups.
Intermolecular hydrogen bonds link molecules into sheets parallel to the bc plane.
The B(OH)(2) and CONH(2) groups are twisted out of the benzene ring plane by approximately 24 degrees.

Conclusions:

The crystal structure reveals a unique arrangement with statistical disorder of functional groups.
Hydrogen bonding dictates the formation of extended sheet architectures.
The observed torsion angles provide insight into the conformational preferences of the molecule in the solid state.