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Alkyl Halides

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...

Acid Halides to Esters: Alcoholysis

Acid Halides to Esters: Alcoholysis

Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:

Chemistry of Carbohydrates

Chemistry of Carbohydrates

Carbohydrates are an essential part of the diet in humans and animals. Grains, fruits, and vegetables are natural sources of carbohydrates that provide energy to the body, particularly through glucose, a simple sugar that is a component of starch and an ingredient in many staple foods. The stoichiometric formula (CH2O)n, where n is the number of carbons in the molecule represents carbohydrates. In other words, the ratio of carbon to hydrogen to oxygen is 1:2:1 in carbohydrate molecules. This...

What is Organic Chemistry?

What is Organic Chemistry?

Organic chemistry is the study of compounds of carbon called organic compounds. Organic compounds either originate from living organisms or are synthesized by chemists. A defining trait of these compounds is the presence of carbon as the principal element, which is bonded to other carbon atoms and other elements such as hydrogen, oxygen, nitrogen, and sulfur. The existence of a wide array of organic molecules is a consequence of carbon atoms’ ability to form up to four strong bonds to...

Acid Halides to Carboxylic Acids: Hydrolysis

Acid Halides to Carboxylic Acids: Hydrolysis

Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...

Mass Spectrometry: Alkyl Halide Fragmentation

Mass Spectrometry: Alkyl Halide Fragmentation

Chlorine isotopes exist as 35Cl and 37Cl in a 3:1 ratio, while bromine isotopes exist as 79Br and 81Br in a 1:1 ratio. The mass spectrum of alkyl halides typically produces two distinct molecular ion peaks, the molecular ion peak, [M], and the molecular ion plus two, [M + 2] peak. The relative heights of these two peaks are proportional to the isotopic abundance ratios of the halide. For example, 2‐chloropropane and 1‐bromopropane display two peaks with relative peak heights in a 3:1 and...

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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

Halide Photoredox Chemistry.

Ludovic Troian-Gautier¹, Michael D Turlington¹, Sara A M Wehlin¹

¹Department of Chemistry , University of North Carolina at Chapel Hill , Chapel Hill , North Carolina 27599 , United States.

Chemical Reviews

|March 12, 2019

Summary

This summary is machine-generated.

Halide photoredox chemistry enables solar energy conversion and fundamental studies of electron transfer. This review covers recent advances in iodide, bromide, and chloride photoredox reactions for applications like hydrogen production.

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Area of Science:

Photochemistry
Inorganic Chemistry
Physical Chemistry

Background:

Halide photoredox chemistry is crucial for solar energy conversion, including hydrogen production and power generation.
It offers a unique pathway for studying one-electron transfer processes coupled with halogen bond dynamics.
Understanding the solution chemistry of iodide (I), bromide (Br), and chloride (Cl) is key to advancing this field.

Purpose of the Study:

To provide a comprehensive background on halide photoredox chemistry.
To review recent research and advances in the field.
To guide future research directions.

Main Methods:

Review of existing literature on halide photoredox chemistry.
Discussion of reactions initiated by various charge-transfer excited states (outer-sphere, halide-to-metal, metal-to-ligand).
Analysis of metal halide complexes and their role in hydrogen halide (HX) splitting.

Main Results:

Exploration of Kosower's salt as an early example of an outer-sphere charge-transfer excited state.
Description of numerous transition and main group metal halide complexes with potential for HX splitting.
Detailed examination of long-lived charge-transfer excited states involved in redox reactions with halogens.

Conclusions:

Halide photoredox chemistry has significant practical and fundamental implications.
Recent advances showcase promising new materials and reaction mechanisms.
Future research should focus on key goals to further elevate the field.