Acid catalyzed dehydration of 2 methylcyclohexanol. Acid 2022-10-22

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Acid catalyzed dehydration experiment opportunities.alumdev.columbia.edu

acid catalyzed dehydration of 2 methylcyclohexanol

From a regioselectivity perspective the results make sense; according to Zaitzev, 1-methylcyclohexane should have the higher yield since it has the most stable carbon. Graph 1§ Abundance 0 Time References: Pavia, D. If it proceeds by E1 reaction mechanism, it produces 1-methylcyclohexene while the E3 reaction mechanism gives 3-methylcyclohexene. However the dried product reacted with both bromine and potassium permanganate. This is because 3- methylcyclohexane has a lower boiling point 104°C than 1-methylcyclohexane 110°C and eluted through the column faster.

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14.4: Dehydration Reactions of Alcohols

acid catalyzed dehydration of 2 methylcyclohexanol

The second method is another example in which an intermediate sulfonate ester confers halogen-like reactivity on an alcohol. In this experiment 2-methylcyclohexanol was dehydrated in order to create two alkene products; 1-methylcyclohexene and 3-methylcyclohexene. In the acid catalysed dehydration of 2-methylcyclohexanol, the intermediate step, which is the rate determining step, produces 1-methylcyclohexene, an unsaturated cycloalkene which is more stable with the loss of water. Under acid-catalyst such as sulfuric or phos- phoric acids, the alcohol reacts to lose a wa- ter molecule leading to formation of alkenes. Throughout the process the still head temperature was continually monitored, when a noticeable drop in temperature occurred the heat source was removed.

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Acid

acid catalyzed dehydration of 2 methylcyclohexanol

The second test for §Graph 1 compares the abundance of each product y-axis to the progress of the reaction x- axis. The dehydration takes place via simple distillation to yield product mixtures of 1-methyl cyclohexene and 3- methyl cyclohexene. The mixture was heated up at a controlled rate, in order for it to be collected slowly in the Hickman well still. Note: With the secondary carbocation adjacent a tertiary carbon center, a 1,2 hydride shift rearrangement would occur to form a tertiary carbocation and vcompound below would be the major product. A potential source of error may have been utilizing simple distillation rather than fractal.

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Acid

acid catalyzed dehydration of 2 methylcyclohexanol

However, when bromine was added to the dried product, the red color of the bromine solution was discharged and the solution was completely clear. Our product only contained two of the stereoisomers of 2- methylcyclohexanol, not three. Afterwards all of the alkene mixtures were dried with anhydrous calcium chloride, and then each sample was massed. The two possible outcomes of the mechanism are demonstrated below: Generally a 1,2-hydride shift also known as the Evelyn Effect would have also been an option as a second minor product. Acid- Catalyzed Dehydration of 2-methylcyclohexanol Experiment ABSTRACT Acid-catalyzed dehydration is a common way to synthesize an alkene from alcohol.


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Dehydration Reaction of 2

acid catalyzed dehydration of 2 methylcyclohexanol

After the distillation, the regioselectivity of the compound was found through GC. Since the reaction is carried out under thermodynamic conditions, the most stable alkene is the expected major product. The rate determining step for E1 is an intermediate that is formed when protonation of the hydroxyl group occurs to form H3O+ followed by electrophilic attack on the carbocation formed to absorb the hydrogen making the carbon atom -CH2 and forming a double bond between. Two conical vials were labeled and weighed. The number of plates of 1-methylcyclohexane was also greater than the number of plates of 3-methylcyclohexane. For the example below, the trans diastereomer of the 2-butene product is most abundant.

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Experiment 7 Lab Report

acid catalyzed dehydration of 2 methylcyclohexanol

Additinally, trans alkenes are more stable than cis alkenes and are also the major product formed. Then the conjugate base, HSO 4 —, reacts with one of the adjacent beta hydrogen atoms while the alkyloxonium ion leaves in a concerted process, forming a double bond. GC analysis indicated that the major product was 1-methylcyclohexene and that the minor product was 3-methylcyclohexene. Introduction: The objective of this lab was to complete the dehydration reaction of a 2-methylcyclohexanol. Less 3-methylcyclohexane is formed than 1-methylcyclohexane. The lone pair of electrons on oxygen atom makes the —OH group weakly basic. The mechanism rate of alcohols varies accordingly to their classification.

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The rate

acid catalyzed dehydration of 2 methylcyclohexanol

Mechanism for the Dehydration of Alcohol into Alkene Different types of alcohols may dehydrate through a slightly different mechanism pathway. The peaks on the chromatogram were identified and the retention time tr and the number of theoretical plates N were determined for each peak. Answer: 1-methylcyclohexene which is the major intermediate product Explanation: The rate-determining step of a chemical reaction is often the slowest step of a series of steps in that reaction. The percent composition of the alkenes in the product was then determined. In the third part of the experiment, 0 μL of the dried product was injected into the gas chromatograph and the injection point was marked. A carbocation rearrange- ment in alcohol involves a hydride shift dur- ing which a hydrogen next to a positively charged carbon moves to that carbon, taking its bonding electron pair along with it. Recall that according to Zaitsev's Rule, the more substituted alkenes are formed preferentially because they are more stable than less substituted alkenes.

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Chem 333L Dehydration opportunities.alumdev.columbia.edu

acid catalyzed dehydration of 2 methylcyclohexanol

Dehydration reaction of secondary alcohol The dehydration mechanism for a tertiary alcohol is analogous to that shown above for a secondary alcohol. Conclusion The purpose of this experiment was to complete the dehydration of 2-methylcyclohexane, to use GC to identify the major and minor products, and to determine the regioselectivity of 2-methylcyclohexane. The second peak represents 1-methylcyclohexene. However, since the reaction exhibits Evelyn effect, the product distribution largely depends on time. Transition State Step 2ǂ ǂ Step 2Aǂ ǂ ǂ Transition State Step 2Bǂ ǂ ǂ ǂ Procedure: In the first part of the experiment, a microdistillation apparatus was set up and a boiling stone, 1 mL of 2-methylcyclohexanol, and 2 mL of 85% phosphoric acid were added to the bottom of the flask.


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