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Clemmensen reduction

 

 
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Clemmensen reduction
 
 
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The Clemmensen reduction is a chemical reaction
Chemical reaction

A chemical reaction is a process that always results in the interconversion of chemical substances. The substance or substances initially involved in a chemical reaction are called reactants....
 described as a reduction
Redox

Redox describes all chemical reactions in which atoms have their oxidation number changed.This can be either a simple redox process such as the oxidation of carbon to yield carbon dioxide or the reduction of carbon by hydrogen to yield methane , or it can be a complex process such as the oxidation of sugar in the human body through a ser...
 of ketone
Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
s (or aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
s) to alkane
Alkane

Alkanes, also known as paraffins, are chemical compounds that consist only of the elements carbon and hydrogen , wherein these atoms are linked together exclusively by single bonds without any cyclic structure ....
s using zinc
Zinc

Zinc is a metallic chemical element with the symbol Zn and atomic number 30. It is a first-row transition metal of the group 12 element of the periodic table....
 amalgam
Amalgam

Amalgam may refer to:* Amalgam , mercury alloy* Amalgam , material of "silver" tooth fillings* Amalgam Comics, publisher* Amalgam, Gauteng, South Africa...
 and hydrochloric acid
Hydrochloric acid

Hydrochloric acid is the solution of hydrogen chloride in water. It is a highly corrosive, strong acid mineral acid and has major industrial uses....
. This reaction is named after Erik Christian Clemmensen
Erik Christian Clemmensen

Erik Christian Clemmensen was a Danish-American chemist. He was born in 1876 in Odense, Denmark, and died on May 21, 1941.Clemmensen studied at Polytechnical University in Copenhagen....
, a Danish chemist.

Several reviews have been published.

The Clemmensen reduction is particularly effective at reducing aryl
Aryl

In the context of organic molecules, aryl refers to any functional group or substituent derived from a simple aromatic ring, may it be phenyl, thiophene, indole, etc ....
-alkyl
Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
 ketones.






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Encyclopedia


The Clemmensen reduction is a chemical reaction
Chemical reaction

A chemical reaction is a process that always results in the interconversion of chemical substances. The substance or substances initially involved in a chemical reaction are called reactants....
 described as a reduction
Redox

Redox describes all chemical reactions in which atoms have their oxidation number changed.This can be either a simple redox process such as the oxidation of carbon to yield carbon dioxide or the reduction of carbon by hydrogen to yield methane , or it can be a complex process such as the oxidation of sugar in the human body through a ser...
 of ketone
Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
s (or aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
s) to alkane
Alkane

Alkanes, also known as paraffins, are chemical compounds that consist only of the elements carbon and hydrogen , wherein these atoms are linked together exclusively by single bonds without any cyclic structure ....
s using zinc
Zinc

Zinc is a metallic chemical element with the symbol Zn and atomic number 30. It is a first-row transition metal of the group 12 element of the periodic table....
 amalgam
Amalgam

Amalgam may refer to:* Amalgam , mercury alloy* Amalgam , material of "silver" tooth fillings* Amalgam Comics, publisher* Amalgam, Gauteng, South Africa...
 and hydrochloric acid
Hydrochloric acid

Hydrochloric acid is the solution of hydrogen chloride in water. It is a highly corrosive, strong acid mineral acid and has major industrial uses....
. This reaction is named after Erik Christian Clemmensen
Erik Christian Clemmensen

Erik Christian Clemmensen was a Danish-American chemist. He was born in 1876 in Odense, Denmark, and died on May 21, 1941.Clemmensen studied at Polytechnical University in Copenhagen....
, a Danish chemist.

Clemmensen Reduction Scheme
Several reviews have been published.

The Clemmensen reduction is particularly effective at reducing aryl
Aryl

In the context of organic molecules, aryl refers to any functional group or substituent derived from a simple aromatic ring, may it be phenyl, thiophene, indole, etc ....
-alkyl
Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
 ketones. With aliphatic or acyclic ketones, zinc
Zinc

Zinc is a metallic chemical element with the symbol Zn and atomic number 30. It is a first-row transition metal of the group 12 element of the periodic table....
 metal reduction is much more effective.

The substrate must be stable in the strongly acidic conditions of the Clemmensen reduction. Acid sensitive substrates should be reacted in the Wolff-Kishner reduction
Wolff-Kishner reduction

The Wolff-Kishner reduction is a chemical reaction that fully redox a ketone to an alkane.The method originally involved heating the hydrazone with sodium ethoxide in a sealed vessel at about 200 ?C....
, which utilizes strongly basic conditions. As a result of Clemmensen Reduction, the carbon of the carbonyl group involved is converted from sp2 hybridisation to sp3 hybridisation. The oxygen atom is lost in the form of one molecule of water.

See also

  • Haworth phenanthrene synthesis
  • Wolff-Kishner reduction
    Wolff-Kishner reduction

    The Wolff-Kishner reduction is a chemical reaction that fully redox a ketone to an alkane.The method originally involved heating the hydrazone with sodium ethoxide in a sealed vessel at about 200 ?C....