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UnitV
REACTIONS OF SYNTHETIC
IMPORTANCE
REDUCTION,
OXIDATION and
REARRANGEMENT REACTIONS
REDUCTION
• Reduction of organic molecules has played an important role in
organic synthesis.
• Reduction is referred to as addition of hydrogen to an unsaturated
groups like carbon - carbon double bond or a carbonyl group.
• Typical example of reduction is conversion of ethylene into ethane
CH2=CH2→ CH3-CH3
• The concept of oxidation in terms of oxidation number is also useful
for reduction. In reduction the oxidation number changes from higher
oxidation states to lower oxidation state.
• Examples
Metal hydrides
 The reduction of metal hydrides proceeds by transfer of hydride ion to the
substrate.
 These selectively reduce a number of functional groups such as nitro, carbonyl,
carboxylic acid, nitrile, ester etc., in presence of carbon-carbon double bond.
 A number of complex hydrides have been used for reduction. The most common
are lithium aluminium hydride (LiAlH4) and sodium borohydride (NaBH4).
 These reagents serve as a source of hydride due to the presence of a polar metal-
hydrogen bond.
 Aluminium is less electronegative than boron, the Al-H bond in LiAlH4 is more
polar, thereby, making LiAlH4 a stronger reducing agent.
Mechanism
1) Nucleophilic attack by the hydride anion
2) The alkoxide is protonated
The following table summarizes some important characteristics of these useful reagents.
THANK YOU
Dr. J. THULASIDHASAN
Assistant Professor
Department of Chemistry
PRIST UNIVERSITY
E-mail id : dhasant@gmail.com

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BP401T. PHARMACEUTICAL ORGANIC CHEMISTRY–III Unit V Reactions of synthetic importance

  • 2. REDUCTION • Reduction of organic molecules has played an important role in organic synthesis. • Reduction is referred to as addition of hydrogen to an unsaturated groups like carbon - carbon double bond or a carbonyl group. • Typical example of reduction is conversion of ethylene into ethane CH2=CH2→ CH3-CH3 • The concept of oxidation in terms of oxidation number is also useful for reduction. In reduction the oxidation number changes from higher oxidation states to lower oxidation state. • Examples
  • 3.
  • 4.
  • 5. Metal hydrides  The reduction of metal hydrides proceeds by transfer of hydride ion to the substrate.  These selectively reduce a number of functional groups such as nitro, carbonyl, carboxylic acid, nitrile, ester etc., in presence of carbon-carbon double bond.  A number of complex hydrides have been used for reduction. The most common are lithium aluminium hydride (LiAlH4) and sodium borohydride (NaBH4).  These reagents serve as a source of hydride due to the presence of a polar metal- hydrogen bond.  Aluminium is less electronegative than boron, the Al-H bond in LiAlH4 is more polar, thereby, making LiAlH4 a stronger reducing agent.
  • 6.
  • 7.
  • 8.
  • 9. Mechanism 1) Nucleophilic attack by the hydride anion 2) The alkoxide is protonated
  • 10. The following table summarizes some important characteristics of these useful reagents.
  • 11.
  • 12.
  • 13.
  • 14.
  • 15.
  • 16.
  • 17.
  • 18.
  • 19.
  • 20.
  • 21.
  • 22.
  • 23.
  • 24.
  • 25.
  • 26.
  • 27. THANK YOU Dr. J. THULASIDHASAN Assistant Professor Department of Chemistry PRIST UNIVERSITY E-mail id : dhasant@gmail.com