Acid-Catalyzed Hydration of 1-Hexene

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University of Texas, Rio Grande Valley *

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2123

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Chemistry

Date

Feb 20, 2024

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pdf

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5

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Acid-Catalyzed Hydration of 1-Hexene Objective: The purpose of this experiment is to understand the process of acid-catalyzed hydration by reacting 1-Hexene with water in the presence of an acid catalyst. Converting 1-Hexene into 2-Hexanol by the acid catalyst. While analyzing the product by gas chromatography, IR spectroscopy, and or NMR spectroscopy. Introduction: The goal of this experiment being performed was to have an alkene reaction using 1-hexene for our main material. In order to have a hydration reaction, the alkene compound must be hydrated with water in the presence of an acid as the catalyst. The reason for this experiment to be performed, sulphuric acid was used as our catalyst compound, which donates as a hydrogen. We as well try to accomplish preparing an alcohol using alkene as the key material and lastly, determine the major alcohol component, 2-hexanol. The alcohol compounds are synthesized through hydration of alkenes. This involves net addition to break the bonds of the alkene compound. This creates a carbocation located on carbon number two. Following Markovnikov's rule,the water molecule then attacks the carbocation, causing the oxygen in the water molecule to be electron-deficient. Deprotonation of the oxygen then results in an alcohol on carbon number two. The resulting product is a racemic mixture of 2-hexanol. Procedure:
1. Place 1.0 mL of H2SO4 in a 3mL and adding 0.5 mL of 1-hexene and a magnetic stir bar 2. Place on a stir plate and turn it on for the stirring magnet to stir smoothly at the highest setting for 20 min 3. Add 0.5 mL of 1-hexene to the same solution letting it stir for another 20 min 4. Transfer the solution to a 10 mL Erlenmeyer flask letting it sit to cool down and placing it in an ice bath 5. Measure 4 mL of 9M NaOH in a graduated cylinder and using a pasteur pipet transfer 1mL of 9M NaOH to the vial letting it mix and swirl with the solution placing it in the ice bath right after putting each drop - The solution should have some color change as the time goes by from orange- to pink to light yellow as the NaOH is being added and there should be a solid formed at the bottom 6. Once done with that we will collect the liquid product in the reaction and using the buchner funnel and filter paper we will vacuum it 7. We will measure the mass of a empty 50 mL beaker recording it down and then we will pour the liquid we got after vacuuming and then we will measure the new mass and record it down again 8. Calculate and record the mass of the liquid product. Data sheet: 72.093g (Mass of Crystals and filter paper) - 62.669g (Mass of filter paper)
9.424 g = Actual yield Mass for 1 mole ( 1- Hexene ) = 6 x 12 + 12 = 84 g Mass for 1 mole (hexanol-1) = 6 x 12 + 14 + 16 = 102g 10mL 85% / H2SO4 mass = 85 x 10 / 98.079 = 8.66g Total Reactants used = 8.66 g + 5.00 g = 13.66 g 102 x 5 / 84 = 6.07142857 = 6.07 g hexanol % Theoretical yield = ( 6.07 g / 13.66g) x100 = 44.4 % Theoretical yield = ( actual yield / percentage yield) x 100 21.225 g = (9.424 g / 44.4) x 100 Percent yield = ( actual yield / theoretical yield) x 100 44.400471= 9.424 g /21.225 g 44.4% Mechanism: CH3-CH2-CH2-CH2-CH=CH2—--↑H2SO4↓NaOH-→CH3-CH2-CH2-CH2-CH2-CH2-OH
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