CHEMICAL REACTIONS

CLEMENSEN REDUCTION:
 INTRODUCTION:

• The clemensen reduction is a reaction that is used to reduce aldehydes or ketones to alkanes
using hydrochloric acid and zinc amalgam.

• This alternative reduction involves heating a carbonyl compound with finally divided,
amalgamated zinc in a hydroxylic solvent containing a mineral acid such as HCl.
• The clemensen reduction is named after a Danish Chemist, Erik Christian Clemmensen.
 EXAMPLES OF CLEMMENSEN REDUCTION:

• Clemmensen reduction of prop anal:

• Clemmensen reduction of propanone:

 MECHANISM OF CLEMMENSEN REDUCTION:
CARBANIONIC MECHANISM
• The carbanionic mechanism of reaction
shows that the zinc attacks directly to the
protonated carbon.
CARBENOID MECHANISM
• The carbenoid mechanism is a radical process
and reduces the happenings on zinc metal
surface. The reduction takes place at the
surface of zinc catalyst. In this reaction
alcohols are not postulated as intermediate
because subjection of corresponding alcohol to
these same reactions does not lead to alkanes.
Carbanionic mechanism:
Carbenoid mechanism:
 REACTION CONDITIONS:

• The original conditions reported by clemmensen required using aqueous HCl heated to reflux, so
today milder versions are used.
• For example, the use of powdered zinc in organic solvent such as ether or tetrahydrofuran. These
anhydrous conditions have found great synthetic utility in modern chemistry, such as in the
reduction of a tricyclic ketone in the preparation of anticancer agent.
 STEREOCHEMISTRY AND REGIOSELECTIVITY:

• Stereochemistry:
configuration of the product is reverse so that of reactant. So stereochemistry is in reverse
direction.
• Regioselectivity:
The reaction is SN2, as both reactants are involved in the first step.
Only one product i.e. alkane is produced with reverse configuration.
APPLICATIONS OF CLEMMENSEN REDUCTION:

Conversion:
This reaction has widely used to convert a carbonyl group into a methylene group.
Preparation of substances:
Also important application is the preparation of polycyclic aromatic and aromatics containing
unbranched side hydrocarbon chain.
For reduction:
These reactions are used to reduce aliphatic and mixed aliphatic aromatic carbonyl compounds.
 Specific features of reaction:

• It is a single step reaction.

• No intermediate form.
• Walden inversion occur.
• Transition state is formed which is sp2 hybridized, planner structure.