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Related Concept Videos

Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Physical Properties of Alcohols and Phenols02:32

Physical Properties of Alcohols and Phenols

Alcohols are organic compounds in which a hydroxy group is attached to a saturated carbon. Phenols are a class of alcohols containing a hydroxy group attached to an aromatic ring. The physical properties of the alcohols and phenols are influenced by hydrogen bonding due to the oxygen–hydrogen dipole in the hydroxy functional group and dispersion forces between alkyl or aryl regions of alcohol and phenol molecules.
Alcohols possess a higher boiling point than aliphatic hydrocarbons of similar...
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.
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
Protection of Alcohols02:31

Protection of Alcohols

This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...

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Related Experiment Video

Updated: May 31, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

4-(4-Nitro-phen-oxy)butanol.

Zareen Akhter, Vickie McKee, Muhammad Saif Ullah Khan

    Acta Crystallographica. Section E, Structure Reports Online
    |July 15, 2011
    PubMed
    Summary
    This summary is machine-generated.

    The crystal structure of C(10)H(13)NO(4) reveals intermolecular hydrogen bonding forming supramolecular chains. Additionally, pi-pi stacking interactions were observed between nitro-phenyl groups.

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    Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
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    Published on: August 19, 2013

    Area of Science:

    • Crystal structure analysis
    • Supramolecular chemistry
    • Organic chemistry

    Background:

    • Understanding the intermolecular interactions of organic compounds is crucial for predicting material properties.
    • Crystal structure determination provides fundamental insights into molecular arrangement and bonding.
    • Nitro-aromatic compounds exhibit unique electronic properties influencing their solid-state behavior.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(10)H(13)NO(4).
    • To identify and characterize the intermolecular interactions present in the crystal lattice.
    • To investigate the self-assembly behavior driven by hydrogen bonding and pi-pi stacking.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.
    • Analysis of intermolecular contacts, including hydrogen bonds and pi-pi interactions, was performed.
    • Crystal structure visualization and analysis tools were utilized.

    Main Results:

    • The crystal structure of C(10)H(13)NO(4) was successfully determined.
    • Intermolecular O-H⋯O(nitro) hydrogen bonds were identified, linking molecules into supramolecular chains along the bc diagonal.
    • Significant pi-pi stacking interactions between 4-nitro-phenyl groups were observed, with an inter-planar distance of 3.472(2) Å.

    Conclusions:

    • The crystal packing of C(10)H(13)NO(4) is dominated by a combination of hydrogen bonding and pi-pi stacking.
    • These interactions lead to the formation of extended supramolecular structures.
    • The findings contribute to the understanding of crystal engineering principles for nitro-aromatic compounds.