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Structure and Nomenclature of Alcohols and Phenols

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...

Acidity and Basicity of Alcohols and Phenols

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.

Hydrolysis of Chlorobenzene to Phenol: Dow Process

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...

E2 Reaction: Kinetics and Mechanism

E2 Reaction: Kinetics and Mechanism

SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...

Protection of Alcohols

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...

Structure and Nomenclature of Ethers

Structure and Nomenclature of Ethers

Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent groups, ethers can be classified into two...

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(E)-4-Chloro-2-[(2-hydroxy-phenyl)-iminometh-yl]phenol.

Naser Eltaher Eltayeb, Siang Guan Teoh, Suchada Chantrapromma

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Summary

This study details the crystal structure of a trans-configured C(13)H(10)ClNO(2) compound. It highlights intramolecular hydrogen bonding and intermolecular interactions, revealing molecular packing in the solid state.

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Area of Science:

Crystallography
Organic Chemistry
Solid-State Chemistry

Background:

Understanding molecular structure and intermolecular forces is crucial in chemistry.
Crystal structure analysis provides detailed insights into molecular arrangement and interactions.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(13)H(10)ClNO(2).
To investigate the stereochemistry, hydrogen bonding, and intermolecular contacts within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of bond lengths, bond angles, dihedral angles, and intermolecular interactions.

Main Results:

The compound exhibits a trans configuration around the central C=N bond.
Nearly coplanar benzene rings with a dihedral angle of 2.48° were observed.
An intramolecular O-H⋯N hydrogen bond formed an S(6) ring motif.
Intermolecular O-H⋯O hydrogen bonds resulted in chain formation along the [101] direction.
Short C⋯Cl contacts (3.584–3.646 Å) and an intramolecular C-H⋯O contact were identified.

Conclusions:

The crystal structure reveals specific geometric and bonding features of the title compound.
Intramolecular and intermolecular interactions play a significant role in the compound's solid-state organization.
The findings contribute to the understanding of structure-property relationships in organic crystalline materials.