Key Reactions – Chapter 15

Formation of Organomagnesium
(Grignard’s) and Organolithium Compounds

Reaction of RMgZ and RLi with Proton

Donors

Reaction of a Grignard Reagent with an

Epoxide

Formation of Gilman Reagents

Treatment of a Gilman Reagent with an

Alkyl, Aryl or Alkenyl Halide
Reaction of dichloro- or dibromocarbene
with an Alkene

Simmons-Smith Reaction
Key Reactions – Chapter 16

Reaction with Grignard Reagents

Reaction with Organolithium Reagents

Reaction with Anions of terminal

Alkynes

Reaction with HCN to Form

Cyanohydrins

The Wittig Reaction

 The Horner Emmons-Wadsworth
Modification of the Wittig Reaction

Hydration

Addition of Alcohols to Form

Hemiacetals

Addition of Ammonia and Its Derivatives:

Formation of Imines

Addition of Secondary Amines:

Formation of Enamines
Addition of Hydrazine and Its Derivatives

Keto-Enol Tautomerism

Oxidation of an Aldehyde to a
Carboxylic Acid

Metal Hydride Reduction

Catalytic Reduction
 Reductive Amination

Clemmensen Reduction

Wolff-Kishner Reduction

Deuterium Exchange at an alpha-

Carbon

Halogenation at an alpha-Carbon
Key Reactions – Chapter 25

Formation of Cyclic Hemiacetals

Mutarotation

Formation of Glycosides

Formation of N-Glycosides

Reduction to Alditols
Oxidation to an Aldonic Acid

Oxidation by Periodic Acid