3AL Lecture 8 - Nucleophilic Substitution Reactions You...

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Nucleophilic Substitution Reactions You will be conducting tests to determine whether or not an SN 1 or SN 2 reaction takes place for given 1°, 2° and 3° alkyl halides.
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You Will Work in Pairs and Test 11 Alkyl Halides Br Cl Br 1-Bromopentane 1-Chloropentane 2-Bromopentane Br 3-Bromopentane Br 1-Bromo-2-methylpropane 2-Chloro-2-methylpropane Cl Br 1-Bromo-2,2-dimethylpropane Br Bromocyclopentane Br Bromocyclohexane Br 1-Bromo-adamantane Cl 1-Chloro-adamantane
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The SN 2 Reaction Will Be A Finkelstein Reaction R X + NaI H 3 C CH 3 O R I + NaX • The amount of NaI used in this lab is soluble in the given volume of acetone. • The amount of NaCl and NaBr that might be produced if an SN 2 reaction occurs is insoluble in the given volume of acetone. • If an SN 2 reaction occurs, you will see a precipitate.
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In 11 Test Tubes, You will Test Each Alkyl Halide As Follows Br Precipitate? Time Required to Form? NaI 18% in Acetone NaI H 3 C CH 3 O
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Pay Careful Attention to the Following: The time required to form a precipitate at room temperature. Do your observed results agree with your prediction? • If no precipitate for a given reaction tube and alkyl halide is observed at room temperature after 5-6 minutes, place the reaction tube in a 50° C water bath for 5 minutes (b.p. of acetone?).
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