Lab 6 - Experiment#6 Synthesis of 4-nitrobenzyl azide Objective The purpose of this experiment is to understand the mechanism of S N 2(bimolecular

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CHEM 237 Lab Fall 2009 Objective The purpose of this experiment is to understand the mechanism of S N 2 (bimolecular nucleophilic substitution) reactions through preparation of 4- nitrobenzyl azide from reaction of 4-nitrobenzyl bromide with NaN 5 3 in a polar aprotic solvent. Reagents NaN 3 (sodium azide): nucleophile 4-nitrobenzyl bromide: substrate (benzylic) 10 15 N , N -dimethylformamide (DMF): polar aprotic solvent Diethyl ether: organic solvent for extraction MgSO 4 Apparatus Round bottom flask Drying tube Separatory funnel Filter funnel 20 TLC plate (SiO 2 ) Glass pipette and micropipette Graduate Cylinder (10 mL) Theory 25 30 35 In the S N 2 reaction, a substrate (methyl, benzylic, allylic, primary, or secondary) undergoes nucleophilic attack and displacement of a leaving group via a concerted (one-step) process (Scheme 1). No reaction intermediate such as carbocation and free radical is formed in the S N 2 reaction. Simultaneous bond breaking and making ( concerted ) lead to a
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This note was uploaded on 03/03/2010 for the course CHEM 237 taught by Professor Chong during the Fall '10 term at Illinois Tech.

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Lab 6 - Experiment#6 Synthesis of 4-nitrobenzyl azide Objective The purpose of this experiment is to understand the mechanism of S N 2(bimolecular

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