Convert benzene to benzyl alcohol.

To convert benzene to benzyl alcohol, you can follow a common synthetic pathway known as the Clemmensen reduction. This reduction involves the conversion of an aromatic compound (benzene) to an alkyl group attached to an alcohol (benzyl alcohol). Here's a step-by-step guide to the Clemmensen reduction:

Note: This reaction typically requires anhydrous conditions and careful handling of reagents. It is essential to take appropriate safety precautions and conduct the reaction in a controlled environment.

Materials and Reagents:

Benzene
Zinc amalgam (Zn/Hg)
Concentrated hydrochloric acid (HCl)
Ethanol (absolute or anhydrous)
Water
Ice
Sodium hydroxide (NaOH)
Separatory funnel
Glassware (round-bottom flask, condenser, etc.)
Procedure:

Set up a reflux apparatus consisting of a round-bottom flask, a condenser, and a heating source.

Add a mixture of benzene, concentrated hydrochloric acid (HCl), and zinc amalgam (Zn/Hg) to the round-bottom flask. The ratio of benzene to HCl to Zn/Hg should be approximately 1:2:1 by moles.

Start heating the reaction mixture under reflux (with the condenser attached) and maintain the reflux for several hours (typically around 4-6 hours). The reaction will occur at an elevated temperature.

After the reaction is complete, allow the mixture to cool to room temperature.

Carefully transfer the reaction mixture to a separatory funnel.

Add water to the separatory funnel and shake vigorously to form two distinct layers. The organic layer (containing the desired product) will separate from the aqueous layer.

Drain off the aqueous layer (bottom layer) and keep the organic layer.

To the organic layer (benzyl chloride), add a solution of sodium hydroxide (NaOH) to neutralize any remaining acid. This will also convert benzyl chloride to benzyl alcohol.

The resulting mixture will contain benzyl alcohol in the organic layer.

Isolate benzyl alcohol by either distillation or extraction with a suitable solvent.

If necessary, purify the benzyl alcohol by further distillation or other purification techniques.

Please note that the Clemmensen reduction can be hazardous due to the use of strong acids and mercury in the reaction. It is essential to follow appropriate safety protocols and local regulations when working with these chemicals. Additionally, the disposal of waste containing mercury should be handled according to environmental regulations.