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Types of Enols and Enolates

Types of Enols and Enolates

Aldehydes and ketones form enols, although only about 1% of the enol is present at the equilibrium for simple monocarbonyl compounds. The enol form is undetectable for acetaldehyde, present as only 1.5 × 10−4 % of acetone, and present as only 1.2% of cyclohexanone. Two kinds of regioisomeric enols are possible for unsymmetrical ketones, and their net composition is 1% at equilibrium. This instability is due to the lower bond energy of C=C than the C=O group. The additional instability of enols...

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The chiral α-carbon of the carbonyl compound is the stereocenter of the molecule. As shown in the figure below, when such a carbonyl compound undergoes racemization under an acidic or basic condition, an achiral enol is formed.

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.

Reactivity of Enols

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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...

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The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.

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2-(Prop-2-enyloxy)benzamide.

Bernhard Bugenhagen¹, Yosef Al Jasem, Farah Barkhad

¹Institute of Inorganic Chemistry, University of Hamburg, Hamburg, Germany.

Acta Crystallographica. Section E, Structure Reports Online

|January 4, 2013

Summary

This summary is machine-generated.

This study details the molecular structure of C(10)H(11)NO(2), revealing specific dihedral angles and intramolecular hydrogen bonding. Crystal analysis shows molecules forming tapes via hydrogen bonds and C-H⋯π interactions.

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Area of Science:

Crystallography
Organic Chemistry
Molecular Structure Analysis

Background:

Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
Intermolecular forces, such as hydrogen bonding and pi-pi interactions, play a significant role in crystal packing and material properties.

Purpose of the Study:

To elucidate the detailed molecular conformation and crystal structure of the organic molecule C(10)H(11)NO(2).
To investigate the nature and role of intramolecular and intermolecular interactions in the solid state.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the precise atomic coordinates and bond parameters.
Analysis of dihedral angles, hydrogen bonding networks, and non-covalent interactions (C-H⋯π) was performed.

Main Results:

The benzene ring exhibits distinct dihedral angles with the amide (33.15°) and propen-oxy (6.20°) groups.
An intramolecular N-H⋯O hydrogen bond was observed between the amide and propen-oxy groups.
Crystal packing is dominated by N-H⋯O hydrogen bonds forming tapes, further stabilized by C-H⋯π interactions.

Conclusions:

The molecule C(10)H(11)NO(2) adopts a specific conformation influenced by intramolecular hydrogen bonding.
The observed crystal structure highlights the importance of combined hydrogen bonding and C-H⋯π interactions in directing molecular assembly into tapes.