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Related Concept Videos

Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

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Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
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Hydrogen Bonds01:04

Hydrogen Bonds

9.1K
A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
9.1K
Aldehydes and Ketones with Alcohols: Hemiacetal Formation01:19

Aldehydes and Ketones with Alcohols: Hemiacetal Formation

6.8K
Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
6.8K
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

1.8K
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
1.8K
Acid-Catalyzed Dehydration of Alcohols to Alkenes02:35

Acid-Catalyzed Dehydration of Alcohols to Alkenes

20.7K
In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
20.7K
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

1.9K
The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
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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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Hydrogen Bonding Promotes Alcohol C-C Coupling.

Zhuyan Gao1,2, Junju Mu1, Jian Zhang1

  • 1State Key Laboratory of Catalysis, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian116023, China.

Journal of the American Chemical Society
|October 10, 2022
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Hydrogen bonding stabilizes reactive radicals during photocatalysis, enhancing sustainable chemical production. This method improves the coupling rate and selectivity for producing valuable chemicals like 2,3-butanediol.

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Area of Science:

  • Sustainable Chemistry
  • Photocatalysis
  • Green Energy

Background:

  • Radical intermediates in photocatalysis are highly reactive, leading to side reactions.
  • Sustainable production of chemicals and hydrogen requires controlling these reactive intermediates.

Purpose of the Study:

  • To investigate the role of hydrogen bonding in controlling radical intermediates during photocatalytic reactions.
  • To enhance the selectivity and efficiency of carbon-carbon bond formation using photocatalysis.

Main Methods:

  • Utilized a gold-on-cadmium sulfide (Au/CdS) photocatalyst for ethanol dehydrocoupling.
  • Introduced water to facilitate hydrogen bonding on the catalyst surface and in solution.
  • Analyzed the effects of hydrogen bonding on α-hydroxyethyl radical (αHR) behavior.

Main Results:

  • Hydrogen bonding inhibited oxidation and reverse reactions of αHRs.
  • Water addition increased the αHR coupling rate by 2.4-fold.
  • Selectivity for 2,3-butanediol (BDO) increased from 37% to 57%.

Conclusions:

  • Non-covalent interactions, like hydrogen bonding, can steer radical reaction pathways.
  • Hydrogen bonding offers a strategy for selective photocatalysis and sustainable chemical synthesis.
  • This approach enhances the production of valuable chemicals and hydrogen energy.