chem 230L dehydration of 2-methylcyclohexanol

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Chapman University *

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Chemistry

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Jan 9, 2024

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CHEM 230L: Organic Chemistry I Lab Chapman University Experiment 9: Dehydration 2-Methylcyclohexanol to Form Methylcyclohexenes Intended Learning Outcomes By completing this lab, students will: Understand the theory of how to use the dehydration of alcohols to generate alkene based compounds. Learn how to set up a typical acid catalyzed dehydration reaction. Understand how to analyze basic alkene compounds for the presence of unsaturated carbon-carbon bonds and how to analyze mixtures of isomers via gas chromatography (GC). Synthesize a mixture of alkenes from the dehydration of 2-methylcyclohexanol and analyze the product(s). Introduction This week in lab you use one of the reactions you will about in lecture (Dehydration of alcohols) to synthesize a mixture of 1-methylcyclohexene and 3-methylcyclohexene. As with alkyl halides, alcohols can undergo elimination reactions to form alkenes. However, the alcohol (hydroxy) group by itself is a poor leaving group and must be protonated to form water as a good leaving group. Typically, treatment of an alcohol with acid under heating conditions will allow this reaction to occur. First, acidic conditions allow for protonation of the hydroxy group to generate a good leaving group (water) and heat will then promote an elimination reaction (E1 or E2). The reaction that you will be performing in lab is shown below.
CHEM 230L: Organic Chemistry I Lab Chapman University As this reaction is in equilibrium with the reverse acid catalyzed hydration, the desired dehydration can be favored if the desired product is removed during the reaction. Thus, the reaction is performed using a distillation set-up where the desired product is distilled away as it is formed. After the synthesis and isolation of methylcyclohexes, some simple test will be run to look for the presence of alkenes by seeing if bromine and permanganate can perform addition reactions across the double bond in the desired products. Finally, students will try to determine the ratio of the two isomers formed in the reaction by using Gas Chromatography (GC). Pre-Lab Reading The reading below needs to be completed before the start of lab. 1. Lecture textbook (Klein, 3 trd edition): Sections 12.9 (E1 and E2 Reactions with alcohols section only), pages 532-533. 2. Lecture textbook (Klein, 3 trd edition): Sections 8.9 (halogenation sections only), pages 373-375. 3. Lab textbook (Pavia, 6 th edition): Experiment 24: 4-Methylcyclohexene (introduction only), page 207. 4. Carefully read the procedure for the lab experiment below to ensure that you understand the purpose of each step. Pre-Lab Assignment (15 points) Answer the following questions: 1. Draw a reasonable mechanism for the reaction and formation of both products. (5 pts.)
CHEM 230L: Organic Chemistry I Lab Chapman University 2. Determine how many moles of 2-methylcyclohexanol (MW = 114.2 g/mol) are used in the reaction and then determine the theoretical yield for the methylcyclohexene products (MW = 96.2 g/mol). (5 pts.) 2-methylcyclohexanol (MM = 114.2g/mol; density = 0.93 g/mL) = 5 mL 5 mL * 0.93g/mL = 4.65 g 4.65 g * mol/114.2 g = 4.07*10^-2 mol 96.2g/mol * 4.07*10^-2 mol = 3.92 g of methylcyclohexane products 3. Draw the product(s) that should form in the unsaturation test using Br 2. Explain why the disappearance of the orange color of the solution (due to the presence of Br 2 ) is confirmation that there are unsaturated C-C bonds (alkene or alkynes) present. (5 pts.) Since bromine has a strong attraction for electrons and can undergo addition reactions with alkenes and alkynes (alkenes in this case), the bromine molecule is added across the double bond. Adding bromine to the unsaturated C-C bonds makes the orange color of the bromine disappear, as the bromine is now part of a new compound. Thus, when we see the disappearance of the orange color, it ensures that unsaturated C-C bonds are present and participating in the stated reaction. Procedure Safety: Sulfuric acid is corrosive and harmful and causes skin burns/irritation, serious eye irritation, and respiratory irritation if fumes are inhaled. Wear eye protection, lab coat, and gloves, and work in a hood at all times. 1. In a pre-weighed graduated cylinder (63.860 g), pour 5 mL 2-methylcyclohexanol (mixture of cis-and trans isomers) and determine the mass of the alcohol. Into a 25-mL round bottomed flask equipped with a stir bar, add the 5 mL of 2-methylcyclohexanol, followed by 3 mL of 9M sulfuric acid. Gently swirl the flask to thoroughly mix the liquids. 69.039 g – 63.860 g = 5.179 g
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