The Sandmeyer Reaction Chapter 44 The Sandmeyer Reaction

Purpose In this experiment a separately prepared diazonium salt is combined with copper(I) chloride at 0oC, and then heated to drive the reaction to completeness. Nitrogen gas bubbles off and the diazonium group is replaced with chlorine atom to give the target compound. The final product is purified by sublimation.

Reaction Mechanism The mechanism involves a reduction of the diazonium ion by the cuprous ion, which results in the formation of an aryl radical. In the second step, the aryl radical abstracts halogen from cupric chloride, reducing it and resulting in the final product.

(Moles Product / Moles Starting Material) x 100 = % Yield Comments Follow pp. 600-601 (microscale). Follow the lab handout for all experimental procedures. Wearing rubber gloves is necessary during this lab. You will work with toxic and corrosive compounds. Calculate yield. Moderate to good yields should be achieved. (Moles Product / Moles Starting Material) x 100 = % Yield

Safety 4-Bromoaniline is irritating to eyes, respiratory system and skin. May cause sensitization by skin contact. Do not swallow, do not inhale and avoid contact with eyes and skin. Wear gloves and handle with caution. Copper salts are harmful is swallowed. May cause irritation of respiratory system, do not inhale dust. HCl is corrosive, wear gloves and use caution.