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Mannich Reaction

The document discusses two organic chemistry reactions: Aldol Condensation and Mannich Reaction. Aldol Condensation involves the reaction of aldehydes or ketones to form β-hydroxyaldehydes or β-hydroxyketones, while the Mannich Reaction combines imines from formaldehyde and amines with enolizable compounds to produce β-aminoalkyl carbonyl compounds. The document also outlines the mechanisms and structural requirements for these reactions, as well as their applications.

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abubakar siddique
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564 views10 pages

Mannich Reaction

The document discusses two organic chemistry reactions: Aldol Condensation and Mannich Reaction. Aldol Condensation involves the reaction of aldehydes or ketones to form β-hydroxyaldehydes or β-hydroxyketones, while the Mannich Reaction combines imines from formaldehyde and amines with enolizable compounds to produce β-aminoalkyl carbonyl compounds. The document also outlines the mechanisms and structural requirements for these reactions, as well as their applications.

Uploaded by

abubakar siddique
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd

ORGANIC

CHEMISTR
Y

ORGANIC
CHEMISTRY
Named Organic
Lecture
Reactions : : 17
ALDOL CONDENSATION
Condensation :
Condensations combine two or more molecules, often with the loss
of a small molecule such as water or an alcohol.

Aldol Condensation :
An aldol addition is a condensation reaction between two molecules
of an aldehyde or two molecules of a ketone.
ALDOL CONDENSATION
• When the reactant is an aldehyde, the addition product is a β
-hydroxyaldehyde which is why the reaction is called an aldol
addition (“ald” for aldehyde, “ol” for alcohol).
• When the reactant is a ketone, the addition product is a
β-hydroxyketone
MANNICH REACTION
 Compounds capable of forming an enol react with imines from
formaldehyde and a primary or secondary amine to yield
β -aminoalkyl carbonyl compounds called Mannich bases.

 Reactants:
 a secondary amine
 formaldehyde as its aqueous solution
 catalytic HCl.
 an enolizable aldehyde or ketone
 Product :
 A Mannich base
MANNICH REACTION
Mechanism :
MANNICH REACTION
Mechanism :
 The mechanism involves the preliminary formation of an imine
electrophile , from the amine and formaldehyde.

 Acid also catalyzes carbonyl compound to form its enol form.

 The enol reacts with the electrophile to give the product.


MANNICH REACTION
Structural Requirements :
Amine :
 May be a secondary or primary amine , the reaction continue in
case of primary amine.

 Aldehyde :
 Aldehyde is usually formaldehyde but other aldehydes and ketone
also have been used.
 the basic requirement is , it should be a good electrophile.
MANNICH REACTION
Enol :
• The reactant may be enol or any other compound capable of
enolization.
Examples :
MANNICH REACTION
Application :
Formation of αβ-unsaturated Carbonyl Compounds :
• The mannich reaction normally give hydrochloride salt of mannic
base.
• These salts are usually stable at room temp. but undergo
elimination on heating

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