PRE_LAB_7

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University of Houston *

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2123

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Chemistry

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Feb 20, 2024

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I. Nucleophilic Substitution of Alkyl Halides October 14, 2023 II. Answers to the Pre-Laboratory Questions: 1. Predict the outcome of the two sets of experiments to be carried out with the 11 halides used in this experiment. a. I predict for the groups that will contain sodium iodide in acetone that: i. 1-bromobutane will produce 1 product: insoluble precipitate. ii. 2-bromobutane will produce 1 product. iii. 2-bromo-2-methylpropane will produce no product. iv. Bromobenzene will produce no product. v. 1-chlorobutane will produce 1 product. vi. 2-chlorobutane will produce no product. vii. 2-chloro-2-methylpropane will produce 1 product. viii. 1-chloro-2-butene will produce no products. b. I predict for the groups that will contain ethanolic silver nitrate that: i. 1-bromobutane will produce 1 product. ii. 2-bromobutane will produce 1 product. iii. 2-bromo-2-methylpropane will produce 1 product. iv. Bromobenzene will produce 1 product. v. 1-chlorobutane will produce no product. vi. 2-chlorobutane will produce no product. vii. 2-chloro-2-methylpropane will produce 1 product. viii. 1-chloro-2-butene will produce no product. III. Purpose: The purpose of this experiment is to explore how changing leaving groups, solvent polarity, temperature, and structure affects nucleophilic substitution of alkyl halides. As well as identifying whether these reactions occur due to SN1 or SN2 will help me understand these mechanisms from the lecture even more. IV. Reactions:
V. Table of Physical Constants: Substance: Molecular Weight (g/mol) Melting Point ( ) Boiling Point ( ) Density (g/mL) Hazards Sodium Iodide 149.89 661 1,304 3.5 Irritant Acetone 58.08 -94.0 56.0 0.79 Irritant Silver Nitrate 169.87 212 440 4.350 Staining and slightly toxic 1- bromobutane 137.02 -112.5 100-104 1.276 Flammable and toxic 2- bromobutane 137.02 -112 91 1.26 Irritant 2-bromo-2- methylpropane 137.02 -20 71-73 1.18 Flammable and irritant Bromobenzen e 157.01 -30.72 156 1.491 Flammable and irritant 1- chlorobutane 92.57 -123 77-78 0.89 Flammable and irritant 2- chlorobutane 92.57 -140 68-70 0.873 Flammable and irritant 2-chloro-2- methylpropane 92.57 -25 51-52 0.851 Flammable and irritant 1-chloro-2- butene 90.55 -65 63.5 (cis) 68 (trans) 0.923 Flammable
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