Dehydration of 2-Butanol by Concentrated Sulfuric Acid into butenes: 1-butene, trans-2-butene, and cis-2-butene Angela Snow Dr.

David Dalton Chemistry 2921 19 October 2009

Introduction: The purpose of this experiment was to demonstrate that when a compound goes through an acid catalyst reaction and forms a secondary carbocation, there are a variety of pathways to complete the reaction. For this experiment, 2-butanol was dehydrated using concentrated sulfuric acid and the products formed were 1-butene, cis-2-butene, and trans-2-butene. This reaction is classified as an E1 elimination reaction. E1 elimination reactions form an intermediate carbocation. For the formation of an alkene from a hydrated carbocation, a proton is generally lost and a leaving group. It is called an elimination reaction because a small group is eliminated from the molecule; when the leaving group is water, the molecule is then called dehydrated. The reactivity of an alcohol is directly related to the stability of the intermediate carbocation. When this reaction happens, the alcohol is first protonated to form an oxomium ion which is then forms the intermediate carbocation. Once the carbocation is formed, which then generates a variety of possibilities for a product. All of these steps occur in equilibrium conditions.

Results: Figure 1: Gas Chromatograph of Products from Dehydration of 2-butanol

There are three small peaks on the gas chromatograph located just after each other. It is experimentally shown that the gasses elute from the GC in the order of 1-butene, trans-2-butene and cis-2-butene. On the gas chromatograph, the second peak appears slightly larger than the first and the second which is supposedly the major product due to experimental analysis. Error Analysis: One of the possible sources of error for thir experiment occurs with the collection apparatus and the injection of the collected gas into the gas chromatograph. Because of the caps used to for the reaction vessel, there is possibility of several holes in the cap allowing for some of the product gas to escape which results in a loss of product. Additionally, if only one GC experiment is done with the collected gas, the largest peak on the chromatograph may be the first immediate peak which is are and could be mistaken for one of the products if a second GC is not run. Discussion: For this experiment, the compound 2-butanol was dehydrated using concentrated sulfuric acid and the products 1-butene, trans-2-butene, and cis-2-butene resulted. The apparatus was set up by heating the mixture of 100microliters of 2-butanol and 50microliters combined in a small conical vial. The vial is then heated in a sand bath and attached with a cannula to a gas collection apparatus. The gas collection apparatus was set up by filling a beaker of water and inverting a vial in the water for it to become filled with water. The top of the vial is covered with a septum and the vial is then covered with a finger and turned upside down and inserted into the beaker full of water. This is done to keep the water inside the vial so that when the gas flows through the cannula it will push the water out of the vial to indicate the gaseous product is present in the vial. When the vial is inverted in the water filled beaker, the second end of the cannula is inserted through the septum attached to the top of the vial. For the experiment to proceed, the sand bath was then heated to a temperature range of 110oC120oC. The reaction vial was heated in the sand bath and constantly stirred using a magnetic stirrer. As the reaction proceeds, a gas evolves from the reaction and is carried to the gas collection vial through the cannula. Once it reaches the collection vial, the water begins to flow out of the vial into the beaker, this is evident from the bubbles coming from the water filled beaker. Once the gas is collected in the vial, a syringe is inserted through the septum next to the cannula and the gas taken from the vial. When it is removed, it is carried and inserted directly into the Gas Chromatography machine. The gasses are experimentally shown to elute in the order of 1-butene, trans-2-butene, and cis-2butene. It is also experimentally determined that the most substituted carbon will provide the most stable product which will end up to be the major product. In the case of 2-butanol, the carbocation can form at the first carbon creating a primary carbocation which will create 1-butene. The carbocation can also appear at the second carbocation to form both the cis-2-butene and the trans2-butene, but it trans molecules are found to be more thermodynamically stable causing the major product to be trans-2-butene. In all about 4mL of the gas were collected in the collection vial.

Conclusion: For the conclusion of this experiment, three products were obtained from the dehydration of 2butanol. It is believed that the product obtained were 1-butene, trans-2-butene, and cis-2-butene. Although the products cannot be directly identified, it is experimentally determined that the trans2-butene product from the reaction of 2-butanol and concentrated sulfuric acid should be the major product. It has also been experimentally determined that the trans-2-butene elutes as the second peak on the gas chromatograph which did appear slightly larger than the other two peaks. This would further support the hypothesis that the trans-2-butene is the major product. In addition because three peaks appear on the gas chromatograph it indicates at least three gaseous products as end results of the reaction. Experimental Procedure: Collection of Gaseous Products: A vial with the top covered by a septum and an open bottom is inverted with the septum down into a water filled beaker. The vial is then filled with water and inverted again holding a finger over the vial opening to keep water from filling out. A cannula is then inserted into the septum and the other end is inserted into the cap of the reaction vessel. The reaction vessel is heated to a temperature range of 110oC and 120oC from which the gaseous products will evolve and travel through the cannula into the collection vessel. References: 1. Mayo, Pike, and Trumper. Microscale Organic Laboratory. 4th ed. Wiley, 2000. Print.