1-Butanol And 2-Bromobutane Lab Report

This lab will allows the comparison between elimination reactions under acidic and basic conditions through an analysis of two separate reactions: an acid-catalyzed dehydration of 1-butanol and 2-butanol using sulfuric acid and a dehydrobromination under basic conditions using potassium tert-butoxide of 1-bromobutane and 2-bromobutane. The products of all four reactions will be analyzed with gas chromatography, which separates organic compounds to see how each reaction’s product are formed under the constraints of stereochemistry and regiochemistry.
In a general elimination reaction, an atom or group of atoms is removed from a carbon, along with an adjacent hydrogen, resulting in a C=C π bond forming between the α-carbon (where the leaving group was attached) and the β-carbon (where the adjacent hydrogen bond was attached). The first
The dehydrobromination of a secondary and primary bromide followed the convention of Hofmann’s Rule through an E2 elimination because of the presence of a strong, bulky base and resulted in the major product of 1-butene. The acid-catalyzed hydration of a primary and secondary alcohol followed the convention of Zaitsev’s Rule proceeded with E1 elimination for the secondary alcohol. 1-butanol could not proceed with E1 because the unstable primary carbocation would have to undergo a 1,2-hydride or 1,2-methyl shift to proceed, and an E2 elimination is more efficient. The major product for 2-butanol was 2--butene, and for 1-butanol was 1-butene. The results were skewed from the predictions as a result of contaminants present in the product. Instead of gas chromatography, mass spectroscopy could be