Preparation Alkanes 1. Alkanes are usually prepared through the catalytic reduction of alkenes.

An alkene is converted to an alkane when passed with hydrogen over nickel heated at 200 - 300C.

(alkene) for example, CH = CH | | + 2 CH = CH (cyclobutadiene)

(alkane)

(cyclobutane)

2. Other methods of preparation are: a. decarboxylation of a carboxylic acid or its salt b. Wurtz reaction 3. When a mixture of a carboxylic acid (or its sodium salt) is heated with a soda lime (a mixture of calcium oxide and sodium hydroxide), carbon dioxide is eliminated. The process is known as decarboxylation. RCOOH + 2NaOH RH + + (carboxylic acid) (alkane) RCOONa + CaO RH + Ca (sodium (alkane) carboxylate) for example, methane from decarboxylation of sodium ethanoate:

*Note - the alkane produced has less carbon atoms compared to the original carboxylic acid or carboxylate salt used. - benzene can also be prepared from the decarboxylation of sodium benzoate. -however, other sodium salts decompose to form various products. Hence, this is not a useful general method for the preparation of alkanes since the separation of the products is usually difficult. ) (44%) (20%) (33%)

4. In a Wurtz reaction, an ethereal solution of an alkyl halide is treated with sodium to form an alkane. 2RX + 2Na R R + 2NaX for example, 2 the Wurtz reaction gives good yields only for even numbered carbon alkanes of high molecular weights. *Note Hydrolysis of Grignard reagents produce alkanes. Grignard reagents are produced when alkyl halides react with magnesium. When treated with water or dilute acid, Grignard reagents decompose to form alkanes. RX + Mg RMgX RH (alkyl halide) (Grignard reagent) (alkane) for example,