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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

Chair Conformation of Cyclohexane

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The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
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¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

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At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...

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Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3 hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...

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Related Experiment Video

Updated: Nov 19, 2025

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

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Published on: July 28, 2018

Fluorinated Rings: Conformation and Application.

Rajarshi Mondal¹, Mohamed Agbaria¹, Zackaria Nairoukh¹

¹Institute of Chemistry, The Hebrew University of Jerusalem, Edmond J. Safra Campus, Jerusalem, 9190401, Israel.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|January 29, 2021

Summary

This summary is machine-generated.

Fluorine substitution significantly alters molecular shape in organic compounds. This review explores how fluorine impacts the conformational preferences of fluorinated aliphatic systems through unique interactions.

Keywords:

carbocycles conformational behavior fluorine functional molecules heterocycles

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Last Updated: Nov 19, 2025

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Area of Science:

Organic Chemistry
Materials Science
Physical Chemistry

Background:

Fluorine incorporation is widespread in chemistry and industry due to unique properties.
Fluorine's impact on molecular conformation, specifically C-F bond orientation, is a key area of interest.

Purpose of the Study:

To review the conformational behavior of fluorinated aliphatic carbo- and heterocyclic systems.
To detail the interactions (charge-dipole, dipole-dipole, hyperconjugative) influencing fluorinated molecule conformations.

Main Methods:

Review of existing literature on fluorinated organic systems.
Analysis of conformational preferences based on intermolecular interactions.
Discussion of stabilization effects in low-energy conformations.

Main Results:

Fluorine substitution introduces specific interactions that dictate conformational preferences.
These interactions stabilize specific low-energy conformations in fluorinated alicyclic systems.
The study highlights recent applications demonstrating these conformational effects.

Conclusions:

Fluorine's influence on conformation is a critical factor in molecular design.
Understanding these interactions enables precise control over molecular shape and properties.
This knowledge is crucial for advancing applications in various scientific fields.