Preview

Alkene Fron an Alcohol: Cyclohexene Synthesis from Cyclohexanol

Powerful Essays
Open Document
Open Document
1506 Words
Grammar
Grammar
Plagiarism
Plagiarism
Writing
Writing
Score
Score
Alkene Fron an Alcohol: Cyclohexene Synthesis from Cyclohexanol
Cyclohexene Synthesis by Dehydration Reaction of Cyclohexanol Gjulia Vokrri 02-15-2013

Abstract
Alkenes can be produced by heating and dehydrating an alcohol in the presence of a strong acid.
The purpose of this experiment was to synthesize cyclohexene by dehydration of cyclohexanol and to detect the presence of a double bond in the alkene. The dehydration reaction using distillation was performed using two acid catalysts, 85% phosphoric acid and sulfuric acid. Tests for unsaturation were performed adding drops of bromine in tetrachloride and potassium permanganate to four test tubes, two containing 5 drops of cyclohexanol(control), and two containing cyclohexene(prepared product. 3 drops of bromine solution changed the product from red to clear within in 5 seconds. The control remained red after 5 drops of bromine were added. Likewise, 3 drops of potassium permanganate changed the product from purple to brown within 3 seconds. The control remained purple after 5 drops were added. These positive results both theoretically and experimentally confirmed the presence of a double bond by comparing the control and the product to their changes or lack of changes in color.

Introduction
Alkenes are unsaturated hydrocarbons that contain at least one double bond (Brown et al. 2012). The presence of the double bond allows alkenes to react in a variety of ways. Economically they are very important (Thornley 2011). They are used in the petrochemical industry to refine and process petroleum, which are many of the fuels used in airplanes and cars and machinery. They can polymerize to form polymers, which form many different types of plastics such as rigid water pipes, plastic bottles, elastic rubber, and many household items. One way to synthesize an alkene is to perform an alcohol dehydration reaction using acid catalysts. The goal



References: Brown, William. Foote, Christopher. Iverson, Brent. Ansylyn, Eric. Novak, Bruce. “Organic Chemistry”, 6th ed. Brooks/Cole 2012. p 186-200. Ophardt, Charles.”Polymers” (http://www.elmhurst.edu/~chm/vchembook/400polymers.html) , 2003. Pavia, Donald. Lampman, Gary. Kriz, George, Engel, Randall. “A Small Scale Approach to Organic Laboratory Techniques”, 3rd ed. Mary Finch2011. p 179-182, 719-726. Saenz, Aaron.” Sony’s New Flexible OLED Display Can Roll Into Tiny Cylinder While Playing!” (http://singularityhub.com/2010/05/29/sonys-new-flexible-oled-display-can-roll-into-tiny-cylinder-while-playing-video/) 2010. Thornely, Richard. ”Outline the Economic Performance of the reactions of Alkenes IB Chemistry” (http://www.youtube.com/user/richardthornely), 2013.

You May Also Find These Documents Helpful

  • Satisfactory Essays

    CHM 237 Lab 10 Report

    • 757 Words
    • 3 Pages

    To synthesize 4-methylcyclohexene from 4-methylcyclohexanol the starting material can be dehydrated resulting in the desired compound. For dehydration to be possible the OH group on the 4-methylcyclohexene must first be converted into H2O by means of an acid-base reaction using a strong acid catalyst such as phosphoric acid and sulfuric acid. The H2O will then become the favored leaving group and leave on its own resulting in the formation of a carbocation in excess water. The water will remove the acidic hydrogen on the carbocation producing the desired alkene as well as regenerating the acid catalyst (fig. 2). A time effective way to collect the 4-methylcyclohexene is to heat the reaction to reflux as it is taking place. This allows the product to be separated from the starting materials by means of the boiling point discrepancy between the isolated alkene (101-102C) and the starting alcohol (171-173C). After the distillate is collected any impurities of water and phosphoric acid can be extracted by adding sodium chloride, drying the resulting organic layer with an anhydrous solid, and filtration. IR of both the starting alcohol and the resulting alkene can be compared as a means of identification and characterization as well as a Br2…

    • 757 Words
    • 3 Pages
    Satisfactory Essays
  • Good Essays

    When the product is formed, you want it to follow Zaitsev’s Rule. When the more stable product of an elimination reaction predominates the reaction is said to obey Zaitsev’s Rule. An E1 m reaction will obey Zaisev’s Rule. In this experiment two forms of alkenes are produced, disubstituted and trisubstituted alkene is more stable than the disubstituted. The di- and tri- are very important to understand. They refer to double bond and how it is attached to whatever number…

    • 774 Words
    • 4 Pages
    Good Essays
  • Good Essays

    In an E1 reaction, where E stands for elimination and 1 stands for unimolecular. The breaking of the C-LV bond is completed before any reaction occurs between the base to lose a hydrogen and form the carbon-carbon double bond [1]. When the more substituted alkene is the dominant product, the reaction follows Zaitsev's rule. Zaitsev's rule states that the major product of a β-elimination reaction is the most stable alkene [1].Acid-Catalyzed Dehydration is the elimination of a molecule of water from adjacent carbon atoms. An alcohol can be converted to an alkene by dehydration, which is often brought on by heating the alcohol with either 85% phosphoric acid or concentrated sulfuric acid [1]. The objective of this experiment is to dehydrate 3-methyl-3-pentanol to obtain the product mixture of isomeric alkenes 3-methyl-2pentene and 2-ethyl-1-butene. Then use the gas chromatography to separate the product mixture and analyze the composition [2].…

    • 1090 Words
    • 5 Pages
    Good Essays
  • Powerful Essays

    To keep it as simple as possible, (K.I.S.S.) this topic involves the study of: 1. POLYMERS FROM PETROCHEMICALS & BIOMASS…

    • 15670 Words
    • 63 Pages
    Powerful Essays
  • Good Essays

    Alkenes are unsaturated hydrocarbons with a carbon-carbon double bond. In a double bond, a pair of electrons lies between the carbon atoms in a σ bond and the other pair of shared electrons lie above and below the plane in a π bond. This electron rich area of the molecule is fairly exposed for electrophilic attack.…

    • 532 Words
    • 3 Pages
    Good Essays
  • Better Essays

    Bisphenol a

    • 1722 Words
    • 7 Pages

    Since 1950, many major consumer production companies have been using BPA in the formation of the plastics of many different products humans use daily. In commercial production, the para, para’ isomer (p,p’) is the preferred product. The ortho, para’- BPA isomer is also produced but in low levels and is removed by recrystallization. BPA can come in the form of a white to tan crystal, flake, or powder. This compound has a mild phenolic odor yet it is not volatile. BPA is not sold directly for consumer use but serves as the raw material that makes up the polymers used to produce consumer products such as polycarbonate and epoxy resins as stated before. ("DOW Chemical Company" 1-14).…

    • 1722 Words
    • 7 Pages
    Better Essays
  • Better Essays

    A Cis to Trans Conversion

    • 1464 Words
    • 6 Pages

    Molecules with double bonds are alkenes, and they have restricted rotation around the double bond so they tend to form the cis and trans geometric isomers. While both of these isomers have the same molecular formula, they usually vary in many physical features. Cis isomers have two identical groups located on the same side of the double bond, while trans isomers have the two groups on opposing sides of the molecule. Trans isomers are usually more stable than cis isomers because there is no steric interaction, or repulsion, between the carboxyl groups of the molecule. The more negative heat of formation value of trans alkenes also show that these compounds are more stable than cis alkenes. In the first part of this experiment, we formed maleic acid from maleic anhydride by adding the maleic anhydride to boiling water and then filtering the product using a Buchner funnel. We then mixed the filtrate with HCl and boiled it to form fumaric acid in the second part of the experiment.…

    • 1464 Words
    • 6 Pages
    Better Essays
  • Good Essays

    Butane, Butene and all isomers that come with them are considered to be alkanes and alkenes respectively. They differ from each other in the fact that Butane contains only single bonds, whereas Butene has both single and one double bond. Regardless of this difference in many situations the two molecules can display similar behaviours.…

    • 509 Words
    • 3 Pages
    Good Essays
  • Good Essays

    ALKENE or alkyne i.e. any non-aromatic unsaturated hydrocarbon with a double or triple carbon-carbon bond.…

    • 1893 Words
    • 8 Pages
    Good Essays
  • Better Essays

    References: - Nic, M.; Jirat, J.; Kosata, B., eds. (2006–). "alkanes". IUPAC Compendium of Chemical Terminology (Online ed.).…

    • 1078 Words
    • 5 Pages
    Better Essays
  • Good Essays

    Alkenes

    • 5090 Words
    • 21 Pages

    Alcohols when heated in presence of H2SO4, H3PO4, P2O5, Al2O3 or BF3 undergo loss of water molecule with the formation of alkene.…

    • 5090 Words
    • 21 Pages
    Good Essays
  • Satisfactory Essays

    Elecrophilic Addition to carbon-carbon double bond Stereochemistry of Elecrophilic addition reaction Hydrogenation of double and triple bond Nucleophilic Addition to carbon-carbon double bond Regio and chemoselectivity…

    • 517 Words
    • 3 Pages
    Satisfactory Essays
  • Powerful Essays

    The first oil deposits in India were found in Digboi, Assam in 1889. That is when India’s journey in the Petroleum Industry began. Post Independence, Oil India Limited was formed which was a joint venture involving the Indian Government and the British owned Burmah Oil Company (presently known as BP) whilst the Indo-Stanvac Petroleum Project in West Bengal was between the Indian Company and the American Company SOCONY-Vacuum (presently known as Exxon Mobil). This changed in 1956 when the government adopted an industrial policy that placed oil as a “Schedule A Industry” and put its future development in the hands of the state. In October 1959 an Act of Parliament was passed which gave the state owned Oil and Natural Gas Commission (ONGC) the powers to plan, organize, and implement programs for the development of oil resources and the sale of petroleum products and also to perform plans sent down from central government.…

    • 1574 Words
    • 7 Pages
    Powerful Essays
  • Satisfactory Essays

    Petrochemicals are used to make plastic, rubber, nylon and other consumer products and are utilized in manufacturing, construction, pharmaceuticals, aviation, electronics and nearly every commercial industry.…

    • 506 Words
    • 3 Pages
    Satisfactory Essays
  • Better Essays

    Analysis of Hydrocarbons 4

    • 1187 Words
    • 5 Pages

    Hydrocarbons are organic compounds that consist of only C and H atoms. They include the alkanes, alkenes, alkynes, and aromatic hydrocarbons. Because of their relatively non-polarity, all hydrocarbons are insoluble in water. When hydrocarbons burn in sufficient oxygen, carbon dioxide and water are the sole products. The main structural difference among hydrocarbon families is the presence of double or triple bonds between carbon atoms. The alkanes are saturated organic compounds, or those with only single bonds. Unsaturated organic compounds are those which have double or triple bonds. [1]…

    • 1187 Words
    • 5 Pages
    Better Essays