Nucleophilic Aliphatic Substitution

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Experiment 8.2: Nucleophilic Aliphatic Substitution: Synthesis of 1-Bromobutane
Reference:
Schoffstall, Allen M., Barbara A. Gaddis, and Melvin L. Druelinger. "Experiment 8.2." Microscale and Miniscale Organic Chemistry Laboratory Experiments. New York: McGraw-Hill Higher Education, 2004. 267-70. Print.

General Procedure:
This experiment was designed to convert 1-butanol to 1-bromobutane by reacting with sulfuric acid and sodium bromide. Protonation of 1-butanol by hydrogen bromide and bromide ions on the alcohol group gave 1-bromobutane. Reflux, purification, and filtering were used to separate out the 1-bromobutane for testing using an GC spectrum and refractive index.
Synthesis of 1-Bromobutane
The compound was synthesized according to Experiment 8.2 from the Microscale and Miniscale Organic Chemistry …show more content…

This was allowed to mix for a few minutes; a little excess water was used to ensure that sodium bromide was fully dissolved. This mixture was placed in an ice bath while continuing to stir. 1.3 ml (24.39 mmols) of concentrated sulfuric acid was added dropwise. The flask was removed from the ice bath and heated to reflux for 1 hour while continuing to stir. The resulting top layer was transferred to a conical vial in which 1.5 mL (22.51 mmols) of 80 % sulfuric acid was added. 2.0 mL of water was added to allow a layer to form. The bottom layer was removed and transferred to another conical vial in which 2.0 mL of saturated sodium bicarbonate was added. The bottom, organic layer, was transferred to a conical vial. Calcium chloride, a drying agent, was used to collect the remaining aqueous layer that

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