Vernier Software and Technology
Vernier Software & Technology

SN2: Synthesis of 1-bromobutane

Introduction

Alkyl halides can be prepared from their corresponding alcohols via an acid catalyzed substitution reaction. The mechanism of these acid catalyzed substitution reactions are labeled as SN1 (substitution, nucleophilic, unimolecular) and SN2 (substitution, nucleophilic, bimolecular). Tertiary alcohols follow the SN1 route, primary alcohols follow the SN2, route and secondary alcohols can follow either path.

The SN2 reaction for converting 1-butanol to 1-bromobutane involves rapid protonation of the alcohol along with a concerted step where the nucleophile attacks the carbon, displacing water. The backside attack by the nucleophile is favored for primary substrates and less ideal for secondary and tertiary substrates.

The product will be verified by gas chromatography by comparing the chromatograms of the starting material, 1-bromobutane standard, and your product. Confirmation of your product, 1-bromobutane can also be performed by reacting the product with a solution of sodium iodide in acetone. The primary alkyl halide will react by means of an SN2 mechanism with the sodium iodide to form an insoluble precipitate. The appearance of a precipitate indicates a positive result suggesting the presence of a primary alkyl halide.

Objectives

In this experiment, you will

  • Synthesize tert-butyl chloride via an SN1 reaction.
  • Confirm the presence of a tertiary alkyl halide using the silver nitrate test.
  • Verify the product by gas chromatography.

Sensors and Equipment

This experiment features the following Vernier sensors and equipment.

Additional Requirements

You may also need an interface and software for data collection. What do I need for data collection?

Organic Chemistry with Vernier

See other experiments from the lab book.

1Determining Melting Temperature
2Recrystallization of Benzoic Acid and Aspirin
3Determination of a Boiling Point: Simple and Fractional Distillation
4Identifying an Unknown Analgesic by Melting Temperature and Thin-Layer Chromatography
5Separation of Organic Compounds by Acid-Base Extraction Techniques
6Understanding Polarimetry
7Identification of Organic Unknowns Using Polarimetry
8Investigating Gas Chromatography
9Fractional Distillation of Esters
10Understanding Intermolecular Forces Using a Gas Chromatograph: Enthalpy of Vaporization
11Investigating Thermodynamic Relationships of Substituted Hydrocarbons
12Extraction of Spinach Pigments and Analysis by Electronic Absorption Spectroscopy
13SN1: Synthesis of t-butyl chloride
14SN2: Synthesis of 1-bromobutane
15Observing the Reaction Kinetics of Sucrose with Polarimetry
16The Synthesis and Analysis of Aspirin
17Isolation and Epoxidation of a Natural Product: Limonene
18Synthesizing Ethyl Acetate by Fisher Esterification
19Synthesis of Dibenzalacetone by Aldol Condensation
20The Diels-Alder Reaction of Anthracene with Maleic Anhydride
21Friedel-Crafts Acylation of Ferrocene
22Grignard Formation of Crystal Violet
23Synthesis of Fluorescein
24Synthesis of Methyl Orange and Its Application to Textiles
25Analysis of Natural Products
26Using a Gas Chromatograph: Identifying an Unknown Compound

Experiment 14 from Organic Chemistry with Vernier Lab Book

<i>Organic Chemistry with Vernier</i> book cover

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