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NUCLEOPHILIC ADDITION REACTION
 A Nucleophilic addition reaction is a chemical addition reaction in which a nucleophile
forms a sigma bond with an electron deficient species. These reaction enable a
conversion of carbonyl groups into variety of function group.
 Aldehydes and ketones give two type of nucleophilic addition reaction.
 They are:
1. Simple without elimination nucleophile reactions.With sodium bisulphite, Grignard, HCN
and Alcohol
2. Nucleophilic addition reactions followed by elimination.
 This reaction is involved by elimination of water molecule. In which first is
 Reaction with ammonia Derivatives
 Reaction with ammonia.
 ADDITION OF GRIGNARD REAGENT
 Grignard reagent are strong nucleophile, they add readily to aldehydes and ketones to
form addition products which form alcohols.
Nucleophilic Addition of carbonyl  compounds.pptx
 ELIMINATION OF WATER MOLECULE
 REACTION WITH AMMONIA DERIVATIVES
Aldehydes and ketones undergo nucleophilic addition reaction with a number of ammonia derivatives
such as hydroxylamine, hydrazine in weakly acidic medium to form addition products which
automatically lose a molecule of water to form compound containing C=N group.
Example:
MECHANISM
 REACTION WITH AMINE
 Most of the aldehydes react with ammonia to form addition products called aldehyde-
ammonias. These products are unstable and immediately lose a molecule of water to
form aldimines which subsequently undergo polymerization.
 Benzaldehyde reacts with ammonia to form a complex product called hydrobenzamide.
 ADDITION OF SODIUM BISULPHITE
 Carbonyl compounds form crystalline adducts with sodium bisulphite.
MECHANISM
 It involves nucleophilic addition at carbonylic carbon
 Since S is the more nucleophilic site than O , therefore a C- S rather than C-O
bond is formed in the adduct. Also, SO3
--- is a large ion and reacts only if C=O
group is not sterically hindered, as in the case of aldehydes, methyl ketones and
cyclic ketones.
 ADDITION OF WATER
 Water ( H-O-H) is a typical nucleophile and adds reversibly to a carbonyl compound to
form a gem –diol ( hydrate).
 The germ diol are too unstable to be isolated. However, the UV and IR data have given
proof about the formation of gem – diols in these reaction.
 ADDITION OF HCN
 Aldehydes and ketones and hydrogen cyanide to give corresponding cyanohydrins. These are
important intermediates in the prepration of hydroxy acid.
Mechanism
 It involves addition of cyanide (nucleophile) followed by addition of
hydrogen.
 ADDITION OF ALCOHOL
 Aldehydes give acetals, when treated with alcohols in the presence of
anhydrous acids. These acetals can regenerate aldehydes o n treatment with
acids and hence its use to protect- CHO group.
MECHANISM
It involves three steps, addition of proton. Nucleophilic addition of R‘OH and
disprotonation to give hemiacetal . Hemiacetal follows same steps further to
give acetal.
Nucleophilic Addition of carbonyl  compounds.pptx
THANKYOU………

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Nucleophilic Addition of carbonyl compounds.pptx

  • 1. NUCLEOPHILIC ADDITION REACTION  A Nucleophilic addition reaction is a chemical addition reaction in which a nucleophile forms a sigma bond with an electron deficient species. These reaction enable a conversion of carbonyl groups into variety of function group.  Aldehydes and ketones give two type of nucleophilic addition reaction.  They are: 1. Simple without elimination nucleophile reactions.With sodium bisulphite, Grignard, HCN and Alcohol 2. Nucleophilic addition reactions followed by elimination.  This reaction is involved by elimination of water molecule. In which first is  Reaction with ammonia Derivatives  Reaction with ammonia.
  • 2.  ADDITION OF GRIGNARD REAGENT  Grignard reagent are strong nucleophile, they add readily to aldehydes and ketones to form addition products which form alcohols.
  • 4.  ELIMINATION OF WATER MOLECULE  REACTION WITH AMMONIA DERIVATIVES Aldehydes and ketones undergo nucleophilic addition reaction with a number of ammonia derivatives such as hydroxylamine, hydrazine in weakly acidic medium to form addition products which automatically lose a molecule of water to form compound containing C=N group. Example:
  • 6.  REACTION WITH AMINE  Most of the aldehydes react with ammonia to form addition products called aldehyde- ammonias. These products are unstable and immediately lose a molecule of water to form aldimines which subsequently undergo polymerization.  Benzaldehyde reacts with ammonia to form a complex product called hydrobenzamide.
  • 7.  ADDITION OF SODIUM BISULPHITE  Carbonyl compounds form crystalline adducts with sodium bisulphite.
  • 8. MECHANISM  It involves nucleophilic addition at carbonylic carbon  Since S is the more nucleophilic site than O , therefore a C- S rather than C-O bond is formed in the adduct. Also, SO3 --- is a large ion and reacts only if C=O group is not sterically hindered, as in the case of aldehydes, methyl ketones and cyclic ketones.
  • 9.  ADDITION OF WATER  Water ( H-O-H) is a typical nucleophile and adds reversibly to a carbonyl compound to form a gem –diol ( hydrate).  The germ diol are too unstable to be isolated. However, the UV and IR data have given proof about the formation of gem – diols in these reaction.
  • 10.  ADDITION OF HCN  Aldehydes and ketones and hydrogen cyanide to give corresponding cyanohydrins. These are important intermediates in the prepration of hydroxy acid.
  • 11. Mechanism  It involves addition of cyanide (nucleophile) followed by addition of hydrogen.
  • 12.  ADDITION OF ALCOHOL  Aldehydes give acetals, when treated with alcohols in the presence of anhydrous acids. These acetals can regenerate aldehydes o n treatment with acids and hence its use to protect- CHO group. MECHANISM It involves three steps, addition of proton. Nucleophilic addition of R‘OH and disprotonation to give hemiacetal . Hemiacetal follows same steps further to give acetal.