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Related Concept Videos

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...
Prochirality02:05

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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...
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.
IUPAC Nomenclature of Aldehydes01:16

IUPAC Nomenclature of Aldehydes

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...

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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2-(Biphenyl-4-yl)propan-2-ol.

Eric Modau1, David C Liles, Petrus H van Rooyen

  • 1Department of Chemistry, University of Pretoria, Private Bag X20, Hatfield 0028, South Africa.

Acta Crystallographica. Section E, Structure Reports Online
|March 14, 2012
PubMed
Summary

This study reveals how a specific organic compound (C15H16O) forms a unique four-molecule structure through hydrogen bonds in its crystal form. This crystal structure differs significantly from its optimized gas-phase conformation.

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Hydrogen bonding plays a crucial role in the self-assembly of organic molecules.
  • Understanding molecular conformation in the solid state is essential for predicting material properties.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound C(15)H(16)O.
  • To investigate the intermolecular interactions and molecular conformation in the solid state.
  • To compare the solid-state conformation with theoretical gas-phase calculations.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the crystal structure.
  • The crystal packing and hydrogen bonding network were analyzed.
  • Gas-phase Density Functional Theory (DFT) calculations were performed for conformational analysis.

Main Results:

  • The title compound C(15)H(16)O crystallizes with two independent molecules in the asymmetric unit.
  • Four molecules form a tetramer through O-H⋯O hydrogen bonds, adopting a specific crystal packing parallel to the c axis.
  • The dihedral angles between aromatic rings in the crystal state (7.96° and 9.75°) are significantly smaller than the DFT-optimized gas-phase conformation (39.33°).

Conclusions:

  • The crystal structure of C(15)H(16)O is characterized by a hydrogen-bonded tetramer.
  • Significant conformational differences exist between the solid state and the gas phase, highlighting the influence of intermolecular forces on molecular geometry.