Amantadine is effective in preventing infections caused by the influenza A virus and in treating established illnesses. It is thought to block a late stage in the assembly of the virus. Amantadine is synthesized by treating 1-bromoadamantane with acetonitrile in sulfuric acid to give Nadamantylacetamide, which is then converted to amantadine. (a) Propose a mechanism for the transformation in Step \(1 .\) (b) Describe experimental conditions to bring about Step \(2 .\)

Acetonitrile acts as a nucleophile and attacks the electrophilic carbon atom of the 1-bromoadamantane. This creates a bond between the nitrogen of the acetonitrile and the carbon of the 1-bromoadamantane, while the bromine atom leaves as a leaving group. At this point, we obtain a positively charged nitrogen atom on the acetonitrile group and a negative charge on the bromine atom.

The proton from the positively charged nitrogen atom is transferred to Br^- which results in the hydrogen atom bonded to the bromine atom. The nitrogen atom then gets a neutral charge. The product obtained is an intermediate imine.

The imine intermediate formed in the previous step undergoes hydrolysis in the presence of sulfuric acid. This causes the imine bond to break and form a carbonyl bond, resulting in the formation of Nadamantylacetamide. (b)

The second step involves converting Nadamantylacetamide to Amantadine. This can be accomplished by a reduction reaction. A suitable reducing agent, such as lithium aluminum hydride (\(LiAlH_4\)), can be used for this purpose.

To bring about the reduction, the following experimental conditions should be followed: 1. Dissolve Nadamantylacetamide in a non-polar solvent like diethyl ether or tetrahydrofuran (THF). 2. Add a stoichiometric amount of lithium aluminum hydride (\(LiAlH_4\)) to the solution and stir it at room temperature for several hours. 3. Carefully quench the reaction mixture by adding water dropwise to the solution to decompose the remaining \(LiAlH_4\). This generates hydrogen gas, so precautions must be taken for safe handling. 4. Separate the organic layer and the aqueous layer by using a separating funnel. 5. Extract Amantadine by evaporating the organic solvent under reduced pressure, followed by purification through techniques like crystallization or chromatography, if necessary. After these steps, we should have Amantadine as the final product.