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Related Concept Videos

Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

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

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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...
Directing Effect of Substituents: ortho–para-Directing Groups01:14

Directing Effect of Substituents: ortho–para-Directing Groups

Ortho–para directors are substituent groups attached to the benzene ring and direct the addition of an electrophile to the positions ortho or para to the substituent. All electron-donating groups are considered ortho–para directors. They donate electrons to the ring and make the ring more electron-rich. The ring is therefore susceptible to the addition of electrophiles. Substituents such as amino, hydroxy, or alkoxy, containing lone pairs on the atom adjacent to the ring, donate electrons...
¹H NMR: Pople Notation01:09

¹H NMR: Pople Notation

The Pople nomenclature system classifies spin systems based on the difference between their chemical shifts. Coupled spins are denoted by capital letters with subscripts indicating the number of equivalent nuclei. When the coupled nuclei have well-separated chemical shifts, they are assigned letters that are far apart in the alphabet, such as A and X. When the difference in chemical shifts is small, coupled nuclei are named using adjacent letters of the alphabet (AB, MN, or XY).
A proton...
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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Published on: August 16, 2018

1,5-Bis(4-nitro-phen-oxy)penta-ne.

Muhammad Saif Ullah Khan, Zareen Akhter, Michael Bolte

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary

    This study details the crystal structure of a C(17)H(18)N(2)O(6) compound. Molecular analysis reveals specific conformations of the connecting chain and slight twists in nitro groups relative to aromatic rings.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure Analysis

    Background:

    • Understanding molecular conformation is crucial for predicting chemical properties and reactivity.
    • The specific arrangement of atoms in crystalline solids provides insights into intermolecular forces and packing efficiency.

    Purpose of the Study:

    • To elucidate the three-dimensional structure of the title compound, C(17)H(18)N(2)O(6).
    • To analyze the conformational details of the pentamethylene chain and the orientation of nitro groups within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the crystal structure.
    • Analysis of bond lengths, bond angles, and dihedral angles provided conformational information.

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    Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
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    Published on: August 16, 2018

    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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    Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
    07:06

    Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

    Published on: November 15, 2017

    Main Results:

    • The compound crystallizes with two molecules in the asymmetric unit.
    • The pentamethylene chain connecting the aromatic rings exhibits both trans and gauche conformations.
    • Aromatic rings are nearly coplanar, with nitro groups slightly twisted out of these planes.

    Conclusions:

    • The determined crystal structure provides a detailed molecular model for C(17)H(18)N(2)O(6).
    • The observed conformations offer insights into the compound's solid-state behavior and potential for intermolecular interactions.