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Unformatted text preview: 3. The compound azidobenzene has the formula C 6 H 5 N 3 , in which the azide functional group (N 3 ) is directly attached to a phenyl group. Azidobenzene reacts with ethylene as shown below, forming a new "heterocyclic" ring. [i.e. a ring with elements other than carbon.] Using the curved arrow formalism, suggest a mechanism for forming the new ring. Hint: It helps tremendously to draw a complete Lewis structure for azidobenzene, showing all formal charges. This reaction forms the basis of click chemistry, a term very recently coined by Nobel Laureate K. Barry Sharpless, and which is making a major impact on drug discovery in the pharmaceutical industry. You can check it out by Googling click chemistry. C 6 H 5 N 3 + H 2 C CH 2 N N N H H H H C 6 H 5...
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This note was uploaded on 03/13/2012 for the course CHEM 2183 at Cornell University (Engineering School).