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Reactivity of Enols

Reactivity of Enols

Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is governed by factors like...

Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation

Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation

This lesson delves into the aldol condensation catalyzed by bases, where aldols undergo dehydration to enals. As shown in Figure 1, the β-hydroxy aldehyde formed in a base-catalyzed aldol addition reaction dehydrates on heating to yield an unsaturated carbonyl product, which is commonly referred to as an enal.

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation

Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation

As shown in Figure 1, under acidic conditions, the β-hydroxy ketone undergoes dehydration via an E1 elimination reaction to form an enone.

Acid-Catalyzed Dehydration of Alcohols to Alkenes

Acid-Catalyzed Dehydration of Alcohols to Alkenes

In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.

Formation of Halohydrin from Alkenes

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.

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Related Experiment Video

Updated: Jun 1, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

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(E)-N'-(4-Hydroxy-benzyl-idene)-4-hydroxy-benzohydrazide methanol solvate.

Cong-Ming Li, Hong-Yan Ban

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study details the crystal structure of a Schiff base molecule with methanol. Hydrogen bonds link these molecules into a 3D network, revealing insights into Schiff base crystal packing.

Area of Science:

Crystallography
Supramolecular Chemistry
Organic Chemistry

Background:

Schiff bases are versatile organic compounds with diverse applications.
Understanding the crystal structure of Schiff base solvates is crucial for predicting their physical properties.
Methanol solvates are common and can influence crystal packing and intermolecular interactions.

Purpose of the Study:

To elucidate the crystal structure of a specific Schiff base-methanol compound.
To analyze the molecular geometry and intermolecular interactions within the crystal lattice.
To describe the formation of the three-dimensional network through hydrogen bonding.

Main Methods:

Single-crystal X-ray diffraction was used to determine the molecular and crystal structure.

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Analysis of bond lengths, bond angles, and dihedral angles provided geometric information.

Intermolecular interactions, specifically hydrogen bonds, were identified and characterized.

Main Results:

The title compound, C(14)H(12)N(2)O(3)·CH(4)O, was successfully synthesized and characterized.
The Schiff base molecule exhibited near planarity with a dihedral angle of 7.2° between benzene rings.
A trans configuration was observed for the methylidene unit.
Extensive hydrogen bonding (O-H⋯O, N-H⋯O, O-H⋯N) resulted in a robust three-dimensional network.

Conclusions:

The crystal structure reveals a stable supramolecular architecture driven by hydrogen bonding.
The presence of methanol as a crystallization molecule influences the packing and network formation.
This structural information contributes to the understanding of Schiff base solvates and their solid-state properties.