Acid catalyzed dehydration of 2 methylcyclohexanol. Dehydration Reaction of 2 2022-10-18

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Acid

acid catalyzed dehydration of 2 methylcyclohexanol

Hint a rearrangement occurs 9. Recall that according to Zaitsev's Rule, the more substituted alkenes are formed preferentially because they are more stable than less substituted alkenes. The product was composed of 78% 1-methylcyclohexane and 22% 3-methylcyclohexane making 1-methylcyclohexane the major product and 3-methylcyclohexane the minor product of the acid-catalyzed dehydration of 2-methylcyclohexanol. This ion acts as a very good leaving group which leaves to form a carbocation. The drastic differences between the two peaks support the material covered about regioselectivity and therefore led to the conclusion that the first peak and therefore major product was 1-methylcyclohexane, which left the second peak and therefore minor product as 3-methylcyclohexane. The second example shows two elimination procedures applied to the same 2º-alcohol.

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Experiment 7 Lab Report

acid catalyzed dehydration of 2 methylcyclohexanol

Because the reaction is E1, it requires a strong acid and heat input to drive the formation of. Mechanism for the Dehydration of Alcohol into Alkene Different types of alcohols may dehydrate through a slightly different mechanism pathway. This reaction was performed under kinetic control and thus the reverse reaction did not take place. Another potential source of error may have occurred in the GC process—since GC is based on polarity rather than identity. If it proceeds by E1 reaction mechanism, it produces 1-methylcyclohexene while the E3 reaction mechanism gives 3-methylcyclohexene.

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Dehydration Reaction of 2

acid catalyzed dehydration of 2 methylcyclohexanol

For the example below, the trans diastereomer of the 2-butene product is most abundant. The purpose of the second part of the experiment was to observe the results of two different tests for unsaturation on the product obtained in the first part of the experiment. Throughout the process the still head temperature was continually monitored, when a noticeable drop in temperature occurred the heat source was removed. 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. However, the general idea behind each dehydration reaction is that the —OH group in the alcohol donates two electrons to H + from the acid reagent, forming an alkyloxonium ion.


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Chem 333L Dehydration childhealthpolicy.vumc.org

acid catalyzed dehydration of 2 methylcyclohexanol

In this case, 1-methyl cyclohexene is theoretically the major product. This is the formation of the minor product. The deprotonated acid the base then reacts with the hydrogen adjacent to the carbocation and form a double bond. The distillate was washed and dried using magnesium sulfate before pro- ceeding to GC analysis. This also requires an acidic catalyst to convert hydroxyl into a good leaving group. The E3 mechanism is similar only that the attack on the carbon atom is done at the -C3 instead of -C1.

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14.4: Dehydration Reactions of Alcohols

acid catalyzed dehydration of 2 methylcyclohexanol

Calculations of retention time and number of theoretical plates are shown in Appendix C. There is a major 1-methylcyclohexene and a minor 3-methylcyclohexene product formed in the reaction. The purpose of the third part of the experiment was to perform gas chromatography on the product and determine the percent composition of the alkenes in the product. GC analysis indicated that the major product was 1-methylcyclohexene and that the minor product was 3-methylcyclohexene. Notice in the mechanism below that the alkene formed depends on which proton is abstracted: the red arrows show formation of the more substituted 2-butene, while the blue arrows show formation of the less substituted 1-butene. Each mixture was analyzed by gas chromatography; the resulting data depicted results for the products of the dehydration of 2-methylcyclohexane, the peaks measured area and retention time.

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Acid catalyzed dehydration experiment childhealthpolicy.vumc.org

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. This weakens the bond and eventually the bond is broken with the electrons going to the oxygen and the carbon now has a positive charge. Fall 2013 Organic Chemistry Laboratory Manual; P. According to this rule, the more substi- tuted alkene will be the major product. Under acid-catalyst such as sulfuric or phos- phoric acids, the alcohol reacts to lose a wa- ter molecule leading to formation of alkenes. Less 3-methylcyclohexane is formed than 1-methylcyclohexane.

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The rate

acid catalyzed dehydration of 2 methylcyclohexanol

This results in two products being formed, one formed in a larger abundance major product than the other minor product. But, in order to specifically avoid this additional variable, simple distillation was used instead of fractal. The dehydration takes place via simple distillation to yield product mixtures of 1-methyl cyclohexene and 3- methyl cyclohexene. Lithium is an element in Group 1 of the Periodic Table. ǂ ǂ ǂ In this reaction of water with the carbocation intermediate, 1-methylcyclohexane is formed as the hydrogen removed is from the carbon that is also bonded to the methyl group. 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.


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Acid

acid catalyzed dehydration of 2 methylcyclohexanol

A potential source of error may have been utilizing simple distillation rather than fractal. L04 Acid-catalyzed Dehydration of 2-Methylcyclohexanol to form 1- methylcyclohexene, 3- methylcyclohexene, or methylenecyclohexane Purpose : The purpose of this lab was to perform an acid catalyzed dehydration of 2- methylcyclohexanol and analyze the yielded structures by GC-MS and IR spectroscopy and the mechanism that leads to their formation. Potassium permanganate solution was added to one test tube of the starting material and one of the dried product. Graph 1§ Abundance 0 Time References: Pavia, D. In the case of 2-methylcyclohexanol, 1-methyl- cyclohexene should be formed as the major product.


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acid catalyzed dehydration of 2 methylcyclohexanol

Reactions: Overall Reaction of Acid-Catalyzed Dehydration of 2-methylcyclohexanol Pictures taken from University of Virginia Organic Chemistry Lab Manual This is an elimination reaction catalyzed by phosphoric acid in which a carbocation intermediate is formed. Note how the carbocation after the rearrangement is resonance stabilized by the oxygen 9. Oxygen can donate two electrons to an electron-deficient proton. This is the carbocation. . In the second part of the experiment, 2-3 drops of starting material were added to two test tubes and 2-3 drops of the dried product were added to two additional test tubes.

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