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Related Concept Videos

Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction01:09

Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction

Wolff–Kishner reduction involves converting aldehydes and ketones to alkanes using hydrazine and a base. The reaction converts a carbonyl group to a methylene group. The method was independently discovered by N. Kishner in 1911 and L. Wolff in 1912. The reduction is carried out in high-boiling solvents such as ethylene glycol and diethylene glycol because heat is required to deprotonate the N–H proton in one of the reaction steps.
Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
Esters to Alcohols: Hydride Reductions01:17

Esters to Alcohols: Hydride Reductions

Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate.
Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

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Scalable Syntheses of Graphene Oxide and Reduced Graphene Oxide using Cascade Design Oxidation and Highly Basic Reduction Reactions
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Epoxide reduction with hydrazine on graphene: a first principles study.

Min Chan Kim1, Gyeong S Hwang, Rodney S Ruoff

  • 1Department of Chemical Engineering, Cheju National University, Cheju 690-756, Republic of Korea.

The Journal of Chemical Physics
|August 21, 2009
PubMed
Summary

This study reveals that hydrazine reduces epoxides on graphene via hydrogen transfer and ring opening, likely through an Eley-Rideal mechanism. Hydrazine derivatives may further lower the reaction barrier.

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Area of Science:

  • Computational Chemistry
  • Materials Science
  • Surface Science

Background:

  • Graphene oxide reduction is crucial for its applications.
  • Hydrazine is a common reducing agent for graphene oxide.
  • Understanding the reduction mechanism is key to optimizing the process.

Purpose of the Study:

  • To elucidate the reaction mechanisms of epoxide reduction by hydrazine on graphene.
  • To investigate the role of hydrogen transfer and ring-opening.
  • To compare potential reaction pathways, such as Eley-Rideal and Langmuir-Hinshelwood mechanisms.

Main Methods:

  • Quantum mechanical calculations.
  • Gradient-corrected spin-polarized density-functional theory (DFT).
  • Analysis of hydrogen transfer and reaction pathways.

Main Results:

  • Epoxide reduction is primarily driven by epoxide ring opening initiated by H transfer from hydrazine.
  • The Eley-Rideal mechanism appears more probable than the Langmuir-Hinshelwood mechanism for this reaction.
  • Formation of hydrazine derivatives during graphene oxide reduction can lower the activation energy for epoxide ring opening.

Conclusions:

  • The study provides detailed insights into the DFT-based mechanisms of epoxide reduction on graphene using hydrazine.
  • The findings highlight the importance of hydrogen transfer and suggest a dominant Eley-Rideal pathway.
  • The role of generated hydrazine derivatives in facilitating the reduction process is emphasized.