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Related Concept Videos

Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

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This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
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Reactions at the Benzylic Position: Oxidation and Reduction00:59

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The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
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NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

10.3K
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

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1.9K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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Phase II Reactions: Methylation Reactions01:17

Phase II Reactions: Methylation Reactions

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Methylation is a phase II biotransformation process involving the attachment of a methyl group to a substrate. Enzymes known as methyltransferases orchestrate this reaction.
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...
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Hydroboration-Oxidation of Alkenes03:08

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10.1K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Methyl 3,5-bis(cyclo-hexyl-meth-oxy)benzoate.

Peter W R Corfield1, Michele L Paccagnini1, Amy M Balija1

  • 1Department of Chemistry, Fordham University, 441 East Fordham Road, Bronx, NY 10458, USA.

Acta Crystallographica. Section E, Structure Reports Online
|May 15, 2014
PubMed
Summary

This study reveals the molecular structure of a specific organic compound (C22H32O4). The molecule is largely flat, with cyclohexyl groups tilted relative to the aromatic core, and forms stacked planar units in crystals.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure Analysis

Background:

  • Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • Aromatic compounds with ester and alkoxy functional groups are common in various chemical applications.

Purpose of the Study:

  • To determine the crystal structure and detailed molecular geometry of the title compound, C22H32O4.
  • To investigate the intermolecular interactions and packing arrangements in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to analyze the crystal structure.
  • Analysis of atomic deviations from planarity and bond angles provided geometric insights.
  • Hydrogen bonding interactions and crystal stacking were examined.

Main Results:

  • The methyl ester and alkoxy oxygen atoms are coplanar with the central aromatic ring (r.m.s. deviation of 0.008 Å).
  • The molecule is essentially planar, excluding the cyclohexyl groups, which are tilted at approximately 30° and 36°.
  • Planar molecular units, linked by C-H⋯O hydrogen bonds, stack along the a-axis with an inter-planar distance of 3.549 Å.

Conclusions:

  • The study provides a precise description of the molecular conformation and crystal packing of C22H32O4.
  • The observed planarity and specific tilting of cyclohexyl groups influence the intermolecular interactions and solid-state architecture.
  • Weak C-H⋯O hydrogen bonds play a significant role in stabilizing the crystal structure.