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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...
10.3K
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

8.3K
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
8.3K
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

11.4K
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
11.4K
Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

4.3K
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.
4.3K
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

3.6K
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...
3.6K
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

9.2K
When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
9.2K

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Benzophenones.

Ashley R Heurung1, Srihari I Raju, Erin M Warshaw

  • 1From the *Department of Dermatology, University of Minnesota Medical School; and †The Department of Dermatology, Veterans Affairs Medical Center, University of Minnesota, Minneapolis, MN.

Dermatitis : Contact, Atopic, Occupational, Drug
|January 11, 2014
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Summary

Benzophenones, common UV filters in sunscreens and cosmetics, can trigger allergic skin reactions like dermatitis and hives. Awareness is crucial due to their increasing prevalence as allergens.

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Area of Science:

  • Dermatology
  • Allergology
  • Cosmetic Science

Background:

  • Benzophenones are widely used as UV filters in sunscreens, cosmetics, and industrial products.
  • These compounds are increasingly recognized for causing adverse cutaneous reactions.

Purpose of the Study:

  • To raise awareness about the potential for benzophenones to induce allergy and photoallergy.
  • To highlight the significance of benzophenones as common allergens in dermatological practice.

Main Methods:

  • Review of clinical cases and scientific literature on benzophenone-induced reactions.
  • Analysis of the role of topical sunscreens, cosmetics, and industrial products as sources of exposure.

Main Results:

  • Benzophenones are documented causes of contact dermatitis, urticaria, and anaphylaxis.
  • Allergy and photoallergy to benzophenones are significant concerns, particularly from cosmetic and sunscreen use.
  • Industrial product exposure can also lead to benzophenone-related reactions.

Conclusions:

  • Benzophenones are significant allergens responsible for various skin reactions.
  • Increased awareness and recognition of benzophenone allergy and photoallergy are essential for patient care.
  • The American Contact Dermatitis Society designated benzophenones as Allergen of the Year 2014 to emphasize this issue.