How does alkyl halide react with ammonia,metallic sodium and dilute caustic potash?
Answers
Explanation:
The alkali metals (Li, Na, K etc.) and the alkaline earth metals (Mg and Ca, together with Zn) are good reducing agents, the former being stronger than the latter. Sodium, for example, reduces elemental chlorine to chloride anion (sodium is oxidized to its cation), as do the other metals under varying conditions. In a similar fashion these same metals reduce the carbon-halogen bonds of alkyl halides. The halogen is converted to halide anion, and the carbon bonds to the metal (the carbon has carbanionic character). Halide reactivity increases in the order: Cl < Br < I. The following equations illustrate these reactions for the commonly used metals lithium and magnesium (R may be hydrogen or alkyl groups in any combination). The alkyl magnesium halides described in the second reaction are called Grignard Reagents after the French chemist, Victor Grignard, who discovered them. The other metals mentioned above react in a similar manner, but the two shown here are the most widely used. Although the formulas drawn here for the alkyl lithium and Grignard reagents reflect the stoichiometry of the reactions and are widely used in the chemical literature, they do not accurately depict the structural nature of these remarkable substances. Mixtures of polymeric and other associated and complexed species are in equilibrium under the conditions normally used for their preparation.
R3C-X + 2Li ——> R3C-Li + LiX An Alkyl Lithium Reagent
R3C-X + Mg ——> R3C-MgX A Grignard Reagent
The metals referred to here are insoluble in most organic solvents, hence these reactions are clearly heterogeneous, i.e. take place on the metal surface. The conditions necessary to achieve a successful reaction are critical.
First, the metal must be clean and finely divided so as to provide the largest possible surface area for reaction.
Second, a suitable solvent must be used. For alkyl lithium formation pentane, hexane or ethyl ether may be used; but ethyl ether or THF are essential for Grignard reagent formation.
Third, since these organometallic compounds are very reactive, contaminants such as water, alcohols and oxygen must be avoided.
These reactions are obviously substitution reactions, but they cannot be classified as nucleophilic substitutions, as were the earlier reactions of alkyl halides. Because the functional carbon atom has been reduced, the polarity of the resulting functional group is inverted (an originally electrophilic carbon becomes nucleophilic). This change, shown below, makes alkyl lithium and Grignard reagents unique and useful reactants in synthesis.