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Organic Reactions and Mechanism

Organic Reactions and Mechanism

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Published by Abhay Kumar Nayak
Chemistry - Organic reactions and mechanism. useful for IITJEE, AIEEE
Chemistry - Organic reactions and mechanism. useful for IITJEE, AIEEE

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Published by: Abhay Kumar Nayak on Apr 27, 2011
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01/04/2014

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Aldol Condensation
In some cases, the adducts obtained from the Aldol Addition can easily be converted (in situ) to α,β
-unsaturatedcarbonyl compounds, either thermally or under acidic or basic catalysis. The formation of the conjugated systemis the driving force for this spontaneous dehydration. Under a variety of protocols, the condensation product canbe obtained directly without isolation of the aldol.The aldol condensation is the second step of theRobinson Annulation. 
Mechanism of the Aldol CondensationAzo Coupling
Azo coupling is the most widely used industrial reaction in the production of dyes, lakes and pigments. Aromaticdiazonium ions acts as electrophiles in coupling reactions with activated aromatics such as anilines or phenols.The substitution normally occurs at the para position, except when this position is already occupied, in whichcase
ortho
position is favoured. The pH of solution is quite important; it must be mildly acidic or neutral, since noreaction takes place if the pH is too low.
Mechanism of Azo Coupling
 
 
Baeyer-Villiger Oxidation
The Baeyer-Villiger Oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, whichconverts ketones to esters and cyclic ketones to lactones. The Baeyer-Villiger can be carried out with peracids,such asMCBPA,or withhydrogen peroxideand a Lewis acid. The regiospecificity of the reaction depends on the relative migratory ability of the substituents attached to thecarbonyl. Substituents which are able to stabilize a positive charge migrate more readily, so that the order of preference is: tert. alkyl > cyclohexyl > sec. alkyl > phenyl > prim. alkyl > CH
3
. In some cases, stereoelectronic orring strain factors also affect the regiochemical outcome.The reaction of aldehydes preferably gives formates, but sometimes only the liberated alcohol may be isolateddue to the solvolytic instability of the product formate under the reaction conditions.
Mechanism of the Baeyer-Villiger Oxidation
 
 
Beckmann Rearrangement
An acid-induced rearrangement of oximes to give amides.This reaction is related to the Hofmann andSchmidt Reactionsand theCurtius Rearrangement,in that an electropositive nitrogen is formed that initiates an alkyl migration.
Mechanism of the Beckmann Rearrangement
Oximes generally have a high barrier to inversion, and accordingly this reaction is envisioned to proceed byprotonation of the oxime hydroxyl, followed by migration of the alkyl substituent "
trans
" to nitrogen. The N-Obond is simultaneously cleaved with the expulsion of water, so that formation of a free nitrene is avoided.
Benzilic Acid Rearrangement

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