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Related Concept Videos

Halogenation of Alkenes02:46

Halogenation of Alkenes

16.7K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
16.7K
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

3.7K
α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
3.7K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

10.4K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
10.4K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

2.9K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
2.9K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

13.5K
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
13.5K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

4.1K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
4.1K

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Synthetic metabolism for biohalogenation.

Antonin Cros1, Gabriela Alfaro-Espinoza2, Alberto De Maria3

  • 1The Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, 2800 Kongens Lyngby, Denmark.

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|December 26, 2021
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Summary

Synthetic biology can now produce organohalides using engineered metabolic pathways. This approach offers an environmentally friendly and cost-effective alternative to traditional chemical methods for valuable chemical synthesis.

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Area of Science:

  • Biotechnology
  • Synthetic Biology
  • Metabolic Engineering

Background:

  • Synthetic biology currently has limitations in accessing diverse molecules.
  • Traditional chemical halogenation is often unspecific and produces hazardous waste.

Purpose of the Study:

  • To explore the potential of synthetic metabolism for biohalogenation.
  • To develop environmentally friendly and economically viable organohalide production methods.

Main Methods:

  • Growth-coupled selection of metabolic modules.
  • Harnessing biosynthetic and biodegradation pathways from environmental bacteria.
  • In vivo biohalogenation strategies.

Main Results:

  • Demonstrated the feasibility of using engineered metabolic modules for biohalogenation.
  • Showcased the potential of environmental bacteria for in vivo halogenation.
  • Established a framework for producing added-value organohalides via biological routes.

Conclusions:

  • Engineered synthetic metabolism offers a powerful platform for sustainable organohalide production.
  • Biohalogenation presents a greener alternative to conventional chemical synthesis.
  • This approach expands the scope of molecules accessible through synthetic biology.