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Related Concept Videos

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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.
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
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...
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).

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Related Experiment Video

Updated: Jul 25, 2026

Induction of Drug-Induced, Autoimmune Hepatitis in BALB/c Mice for the Study of Its Pathogenic Mechanisms
11:36

Induction of Drug-Induced, Autoimmune Hepatitis in BALB/c Mice for the Study of Its Pathogenic Mechanisms

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Butylated hydroxyanisole in perspective.

H Verhagen1, P A Schilderman, J C Kleinjans

  • 1TNO Toxicology and Nutrition Institute, Maastricht, The Netherlands.

Chemico-Biological Interactions
|January 1, 1991
PubMed
Summary

Butylated hydroxyanisole (BHA), a food antioxidant, is carcinogenic in rodents but not genotoxic. Its tumor-forming mechanism may involve reactive oxygen species, crucial for risk assessment in humans.

Area of Science:

  • Food Science
  • Toxicology
  • Carcinogenesis

Background:

  • Butylated hydroxyanisole (BHA) is a synthetic antioxidant widely used in foods to prevent spoilage.
  • BHA's physical, chemical, and antioxidant properties are well-established.
  • Toxicological data, including metabolic fate and carcinogenicity, are reviewed.

Purpose of the Study:

  • To review current knowledge on BHA, focusing on its toxicological aspects.
  • To investigate the mechanism of BHA-induced carcinogenicity, particularly in rodent forestomachs.
  • To inform risk assessment strategies for human exposure.

Main Methods:

  • Literature review of BHA's characteristics, toxicology, and carcinogenicity studies.
  • Analysis of evidence regarding BHA's genotoxicity and epigenetic effects.

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Synthesis of Strong Adhesive Hydrogel, Gelatin O-Nitrosobenzaldehyde
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Synthesis of Strong Adhesive Hydrogel, Gelatin O-Nitrosobenzaldehyde

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Synthesis of Strong Adhesive Hydrogel, Gelatin O-Nitrosobenzaldehyde
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Synthesis of Strong Adhesive Hydrogel, Gelatin O-Nitrosobenzaldehyde

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  • Exploration of potential mechanisms, including the role of reactive oxygen species.

    • Main Results:

    • Sufficient evidence indicates BHA is carcinogenic in rodent forestomachs.
    • BHA shows little evidence of genotoxicity, suggesting an epigenetic mechanism.
    • Reactive oxygen species, like hydroxyl radicals, are implicated in BHA's tumorigenicity.

    Conclusions:

    • BHA is an epigenetic carcinogen whose mechanism of action requires further elucidation.
    • Understanding the thresholded nature of BHA's mechanism is critical for human risk assessment.
    • Further research is needed to determine the precise role of reactive oxygen species and DNA changes in BHA-induced tumors.