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Related Concept Videos

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...
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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Acidity and Basicity of Alcohols and Phenols02:36

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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.
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

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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...
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...

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3,4-Dimeth-oxy-4'-nitro-1,1'-biphen-yl.

Xin-Min Li1, Yan-Jun Hou, Wen-Yi Chu

  • 1College of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 17, 2012
PubMed
Summary

This study details the synthesis of a novel organic compound, C(14)H(13)NO(4), using palladium-catalyzed Suzuki-Miyaura coupling. Structural analysis reveals specific dihedral angles and crystal packing driven by Van der Waals forces.

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Area of Science:

  • Organic Chemistry
  • Crystallography

Background:

  • Suzuki-Miyaura coupling is a vital reaction in organic synthesis.
  • Understanding molecular structure and crystal packing is crucial for material properties.

Purpose of the Study:

  • To synthesize and characterize the title compound, C(14)H(13)NO(4).
  • To elucidate the crystal structure and intermolecular interactions.

Main Methods:

  • Palladium-catalyzed Suzuki-Miyaura coupling reaction for synthesis.
  • X-ray crystallography for structural determination.

Main Results:

  • Successful synthesis of C(14)H(13)NO(4).
  • The asymmetric unit contains two pseudo-inversion related molecules.
  • Specific dihedral angles between aromatic rings and nitro groups were measured (44.30(6)°, 48.50(6)°, 6.54(13)°, and 5.73(10)°).
  • Crystal packing is dominated by Van der Waals interactions.

Conclusions:

  • The study successfully synthesized and characterized a new organic compound.
  • The crystal structure provides insights into molecular conformation and intermolecular forces.