Chapter 28 - Carbon - Carbon bond formation
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How can you form nitriles from haloalkanes?
a. Nitriles can be formed by reacting haloalkanes with sodium cyanide, NaCN, or potassium cyanide, KCN, in ethanol. Through a nucleophilic substitution reaction. b. In this reaction the carbon length of the carbon chain is increased.
How can you produce nitriles from aldehydes and ketones?
a. Aldehydes and ketones will react with hydrogen cyanide in a nucleophilic addition reaction. b. This reaction forms a carbon-carbon bond, thus increasing the number of carbon atoms in the molecule. c. The product is known as a hydroxynitrile. d. Hydrogen cyanide is far too poisonous to use, and an increased reaction rate can be obtained in the presence of cyanide ions. e. A mixture of sodium cyanide and sulfuric acid is used, which improves safety and increases reaction rate.
Describe the reduction of nitriles.
a. Nitriles can be reduced to amines by reacting with hydrogen in the presence of a nickel catalyst. b. 2moles of Hydrogen gas and a Ni catalyst, forms an amine.
Describe the hydrolysis of nitriles.
a. Nitriles undergo hydrolysis to form carboxylic acids by heating with dilute aqueous acid, for example, HCl(aq). b. 2 moles of H20, and HCl to produce carboxylic acid and ammonium chloride.