NuProcedure - Experiment #2 Nucleophilic Substitution...

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Experiment #2 Nucleophilic Substitution REFERENCE: This experiment was adapted from Introduction to Organic Laboratory Techniques, A Microscale Approach , by Pavia, Lampman, Kriz, Engel, 3rd edition. PURPOSE: By reaction equimolar amounts of chloride ion and bromide ion with primary, secondary, and tertiary isomeric alcohols (1-butanol, 2-butanol, and 2-methyl-2-propanol), the relative strengths of the halide nucleophiles and the mechanism of substitution, after forming a protonated alcohol, will be determined. R O H + H + R O H H + R O H H + Nu - + S N 2 S N 1 ? R X + H 2 O The nucleophile solution contains concentrated sulfuric acid, which is very corrosive. Please handle with care! Each student will be assigned the primary or secondary alcohol (either 1-butanol or 2-butanol) as a reactant and all students will react 2-methyl-2-propanol with the chloride ion and bromide ion. Everyone will then analyze the ratio of haloalkanes formed using Gas Chromatography, determine their relative amounts, and share the results with other students. Procedure: Nucleophilic reactions of the halides with 1-butanol, or 2-butanol. 1. Assemble the following microscale reflux apparatus as shown in figure #1 using a 25 mL round-bottom flask, reflux tube, thermometer, and drying tube. 2.
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This note was uploaded on 07/03/2011 for the course CHEM 141 taught by Professor Matt during the Spring '11 term at Edmonds Community College.

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NuProcedure - Experiment #2 Nucleophilic Substitution...

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