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Related Concept Videos

Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
Hydroboration-Oxidation of Alkenes03:08

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.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
Radical Substitution: Allylic Bromination01:27

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...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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.
Regioselectivity and Stereochemistry of Hydroboration02:36

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 stereochemistry.

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Related Experiment Video

Updated: Jun 5, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
06:18

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

5-Bromo-2-methyl-pyridine N-oxide.

Bo-Nian Liu, Shi-Gui Tang, Hao-Yuan Li

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary

    This study details the molecular structure of C(6)H(6)BrNO, revealing bromine displacement and hydrogen bonds. These interactions form centrosymmetric dimers in the crystal structure, influencing molecular arrangement.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • Understanding the precise atomic arrangement in organic molecules is crucial for predicting their chemical and physical properties.
    • Crystal structure analysis provides detailed insights into intermolecular forces and solid-state behavior.

    Purpose of the Study:

    • To elucidate the molecular geometry and crystal packing of the title compound, C(6)H(6)BrNO.
    • To investigate the role of intermolecular interactions in the formation of the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the compound.
    • Analysis of atomic positions and bond lengths/angles provided molecular parameters.
    • Intermolecular interactions, specifically hydrogen bonds, were identified and characterized.

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    Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
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    Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines

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    Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
    06:18

    Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

    Published on: April 24, 2018

    Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
    09:10

    Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities

    Published on: May 27, 2015

    Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
    05:07

    Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines

    Published on: June 23, 2019

    Main Results:

    • The molecular structure of C(6)H(6)BrNO was determined, showing the methyl C and oxide O atoms within the pyridine ring plane.
    • A notable displacement of the bromine atom (0.103(3) Å) from the plane was observed.
    • Intermolecular C-H⋯O hydrogen bonds were identified, linking molecules into centrosymmetric dimers within the crystal structure.

    Conclusions:

    • The crystal structure of C(6)H(6)BrNO is stabilized by intermolecular C-H⋯O hydrogen bonds.
    • These hydrogen bonds lead to the formation of centrosymmetric dimers, dictating the overall crystal packing.
    • The findings contribute to the understanding of structure-property relationships in brominated pyridine derivatives.