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Synthesis of ethene – Dehydration of ethanol

1. Introduction

 Aim:
 To investigate the synthesis of ethene through the dehydration of ethanol and to test the
 product produced using some tests that are characteristic to unsaturated hydrocarbons.

 Hypothesis:
 Write a suitable hypothesis that corresponds to the aim of the experiment.
 ____________________________________________________________
 ____________________________________________________________
 ____________________________________________________________
 ____________________________________________________________

 Example answer:
 Ethene gas will be formed from the dehydration of ethanol and different reactions that
 are characteristic to the alkene will occur in two of the three test tubes, with the third
 test illustrating one of the properties of ethene. The reactions that will occur are
 addition, oxidation and combustion.

 Note: All example answers for this experiment are in italics.

2. Method
 Apparatus and materials list and diagrams:

                                      Materials List
  Wire wool                 Water                                Heat mat
  4 test tubes              Large beaker or trough               Bunsen burner
  100mL small beaker        5 drops of bromine water (Br2)       Ethanol
  Aluminum oxide            5 drops of cold dilute               Stopper with attached
  (Al2O3)                   potassium permanganate               delivery tube
                            solution (KMnO4)
  Retort stand or           Candle                               Retort stand clamp
  wooden clamp
  3 stoppers                Matches


 Note:
 Ethanol is highly flammable and bromine water can be harmful to the skin if in contact
 for long periods. Bromine vapour from bromine water can also be harmful if inhaled.
 Therefore, it is best to wear gloves and go under the fumehood when carrying out the
 bromine part of the experiment.
Safety goggles must be worn throughout the experiment. Unfortunately.


                                     Diagrams:




                           Figure 11: Set up of experiment.

Sequential Steps:

 1. Label three test tubes A, B and C.
 2. Grab a fourth test tube and place a small ball of wire wool in the bottom of that
     test tube. Ensure that the wire wool only covers 1-2cm of the test tube and isn’t
     too compressed.
 3. Pour a small amount of ethanol into the test tube from a beaker, just enough to
     cover the wire wool and allow the ethanol to soak into the wire wool.
 4. Slowly tip the ethanol in the test tube back into the beaker while making sure that
     the wire wool remains at the bottom of the test tube.
 5. Fill the test tube with approximately 5cm of aluminium oxide.
 6. Seal the test tube with the stopper that has the attached rubber hose and either
     attach the test tube to a retort stand or clamp it with a wooden clamp.
 7. Fill up a trough/beaker and test tubes A,B and C with water. Invert test tube A so
     that it is semi-submerged in the trough and set up the experiment as shown in
     figure 1.
 8. Heat the part of the test tube that contains the aluminium oxide until enough
     ethene gas is collected in test tube A. While keeping the Bunsen burner on and in
     place (so that no suck-back occurs), remove test tube A and quickly seal it with a
     stopper. Repeat this heating procedure for test tubes B and C, also sealing them
     with stoppers after collection of the gas.
 9. Add 5 drops of bromine water (Br2(aq)) to the gas in test tube A and replace the
     stopper quickly after. Note down in table 1 any observations on the original and
     final colour of the solution.
 10. In test tube B add 5 drops of potassium permanganate solution (KMnO4) and
     replace the stopper quickly after. Record any observations.
 11. Light a candle, turn test tube C upside down and bring the flame close to the edge
     of the test tube. Record any observations.
3. Results

    Table 1. Qualitative Results
     Test                                    Observations
     Tube
         A


          B


          C




    Table 1. Qualitative Results
     Test                                   Observations
     Tube
         A         Original colour of bromine water - yellow/orange. After a few
                   minutes bromine lost its colour. Final colour - pale yellow
                   and almost clear. The liquid appears oily.
         B         Original colour of Potassium permanganate – purple. Final
                   colour - Brown solution with precipitate in the liquid. Yellow
                   stains were observed on the test tube around the solution.
         C         A yellow flame was observed. The gas burned at the edges of
                   the test tube.

4. Discussion

 Comparison of theoretical and experimental results:
 Compare your qualitative experimental results for each test tube to the theoretical
 results/information in the ‘properties of ethene’ section of your notes. Do your
 experimental results comply with the theoretical results?
 ____________________________________________________________
 ____________________________________________________________
 ____________________________________________________________
 ____________________________________________________________
 ____________________________________________________________

 Yes. The experimental results comply with the theoretical results as in test tube A the
 bromine lost its colour and became pale, in test tube B the purple colour of potassium
permanganate turned into a brown solution and a flame was observed at the edges of
test tube C.

Questions:

   1. Write the equation for the synthesis of ethene through the dehydration of
      ethanol with the organic compounds written in their skeleton structure form.

                       Equation for the dehydration of ethanol.

                        Al2O3



                                                           Dehydration of ethanol
                          occurs                         under the catalyst aluminium
                           oxide to form ethene and steam.

   2. Explain and state the reaction that occurred in test tube A.
       _______________________________________________________
       _______________________________________________________
       _______________________________________________________
       _______________________________________________________
       _______________________________________________________

       An addition reaction occurred in test tube A. The bromine water which was
       originally a yellow/orange colour lost its colour and became pale yellow after
       reacting with ethene. The double bond in ethene was broken and 1,2-
       dibromoethane was formed. This process is also known as halogenation.

   3. Explain and state the reaction that occurred in test tube B.
       _______________________________________________________
       _______________________________________________________
       _______________________________________________________
       _______________________________________________________
       _______________________________________________________

       An oxidation reaction occurred in test tube B. The purple potassium
       permanganate turned brown with precipitate after being added to ethene. This
       is oxidation reaction is characteristic to an alkene, and a dialcohol is formed.
       The colour of the end solution is dependent on the pH conditions of the
       potassium permanganate. Since the product was a brown solution with
       precipitate it can be said that the potassium permanganate solution must have
       been slightly diluted with an alkaline.
4. Name the type of reaction that occurred in test tube C and write a balanced
       equation for the reaction.
        _______________________________________________________
        _______________________________________________________
        _______________________________________________________

                       The reaction was a combustion reaction.
                       Equation for the reaction in test tube C.
                     C2H4 (g) + 3O2 (g)           2CO2 (g) + 2H2O (g)
         Ethene undergoes combustion and forms carbon dioxide and water vapour.

    5. Suggest some other substances other than aluminium oxide that could be used
       as a catalyst for the dehydration of ethanol.
        _______________________________________________________
        _______________________________________________________
        _______________________________________________________

        Sulphuric acid and zeolites are commonly used as catalysts in the manufacture
        reaction of ethene from the dehydration of ethanol.

Conclusion

 Write a suitable conclusion which incorporates the aim and your hypothesis. Ensure
 that a comparison is made to your hypothesis.
 ____________________________________________________________
 ____________________________________________________________
 ____________________________________________________________
 ____________________________________________________________

 Ethene was synthesized from the dehydration of ethanol and was then reacted with
 various reagents to undergo addition, oxidation and combustion reactions as
 hypothesized.
Bibliography

    1) Clark, Jim 2003, Oxidation of alcohols, viewed 1st of October 2010,
       <http://www.chemguide.co.uk/organicprops/alcohols/dehydration.html>
    2) The Nuffield Foundation and Royal Society of Chemistry 2010, Dehydration of
       Ethanol to form ethene, viewed 1st of October 2010,
       <http://www.practicalchemistry.org/experiments/dehydration-of-ethanol-to-
       form-ethene,237,EX.html>

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Ethene practical

  • 1. Synthesis of ethene – Dehydration of ethanol 1. Introduction Aim: To investigate the synthesis of ethene through the dehydration of ethanol and to test the product produced using some tests that are characteristic to unsaturated hydrocarbons. Hypothesis: Write a suitable hypothesis that corresponds to the aim of the experiment. ____________________________________________________________ ____________________________________________________________ ____________________________________________________________ ____________________________________________________________ Example answer: Ethene gas will be formed from the dehydration of ethanol and different reactions that are characteristic to the alkene will occur in two of the three test tubes, with the third test illustrating one of the properties of ethene. The reactions that will occur are addition, oxidation and combustion. Note: All example answers for this experiment are in italics. 2. Method Apparatus and materials list and diagrams: Materials List Wire wool Water Heat mat 4 test tubes Large beaker or trough Bunsen burner 100mL small beaker 5 drops of bromine water (Br2) Ethanol Aluminum oxide 5 drops of cold dilute Stopper with attached (Al2O3) potassium permanganate delivery tube solution (KMnO4) Retort stand or Candle Retort stand clamp wooden clamp 3 stoppers Matches Note: Ethanol is highly flammable and bromine water can be harmful to the skin if in contact for long periods. Bromine vapour from bromine water can also be harmful if inhaled. Therefore, it is best to wear gloves and go under the fumehood when carrying out the bromine part of the experiment.
  • 2. Safety goggles must be worn throughout the experiment. Unfortunately. Diagrams: Figure 11: Set up of experiment. Sequential Steps: 1. Label three test tubes A, B and C. 2. Grab a fourth test tube and place a small ball of wire wool in the bottom of that test tube. Ensure that the wire wool only covers 1-2cm of the test tube and isn’t too compressed. 3. Pour a small amount of ethanol into the test tube from a beaker, just enough to cover the wire wool and allow the ethanol to soak into the wire wool. 4. Slowly tip the ethanol in the test tube back into the beaker while making sure that the wire wool remains at the bottom of the test tube. 5. Fill the test tube with approximately 5cm of aluminium oxide. 6. Seal the test tube with the stopper that has the attached rubber hose and either attach the test tube to a retort stand or clamp it with a wooden clamp. 7. Fill up a trough/beaker and test tubes A,B and C with water. Invert test tube A so that it is semi-submerged in the trough and set up the experiment as shown in figure 1. 8. Heat the part of the test tube that contains the aluminium oxide until enough ethene gas is collected in test tube A. While keeping the Bunsen burner on and in place (so that no suck-back occurs), remove test tube A and quickly seal it with a stopper. Repeat this heating procedure for test tubes B and C, also sealing them with stoppers after collection of the gas. 9. Add 5 drops of bromine water (Br2(aq)) to the gas in test tube A and replace the stopper quickly after. Note down in table 1 any observations on the original and final colour of the solution. 10. In test tube B add 5 drops of potassium permanganate solution (KMnO4) and replace the stopper quickly after. Record any observations. 11. Light a candle, turn test tube C upside down and bring the flame close to the edge of the test tube. Record any observations.
  • 3. 3. Results Table 1. Qualitative Results Test Observations Tube A B C Table 1. Qualitative Results Test Observations Tube A Original colour of bromine water - yellow/orange. After a few minutes bromine lost its colour. Final colour - pale yellow and almost clear. The liquid appears oily. B Original colour of Potassium permanganate – purple. Final colour - Brown solution with precipitate in the liquid. Yellow stains were observed on the test tube around the solution. C A yellow flame was observed. The gas burned at the edges of the test tube. 4. Discussion Comparison of theoretical and experimental results: Compare your qualitative experimental results for each test tube to the theoretical results/information in the ‘properties of ethene’ section of your notes. Do your experimental results comply with the theoretical results? ____________________________________________________________ ____________________________________________________________ ____________________________________________________________ ____________________________________________________________ ____________________________________________________________ Yes. The experimental results comply with the theoretical results as in test tube A the bromine lost its colour and became pale, in test tube B the purple colour of potassium
  • 4. permanganate turned into a brown solution and a flame was observed at the edges of test tube C. Questions: 1. Write the equation for the synthesis of ethene through the dehydration of ethanol with the organic compounds written in their skeleton structure form. Equation for the dehydration of ethanol. Al2O3 Dehydration of ethanol occurs under the catalyst aluminium oxide to form ethene and steam. 2. Explain and state the reaction that occurred in test tube A. _______________________________________________________ _______________________________________________________ _______________________________________________________ _______________________________________________________ _______________________________________________________ An addition reaction occurred in test tube A. The bromine water which was originally a yellow/orange colour lost its colour and became pale yellow after reacting with ethene. The double bond in ethene was broken and 1,2- dibromoethane was formed. This process is also known as halogenation. 3. Explain and state the reaction that occurred in test tube B. _______________________________________________________ _______________________________________________________ _______________________________________________________ _______________________________________________________ _______________________________________________________ An oxidation reaction occurred in test tube B. The purple potassium permanganate turned brown with precipitate after being added to ethene. This is oxidation reaction is characteristic to an alkene, and a dialcohol is formed. The colour of the end solution is dependent on the pH conditions of the potassium permanganate. Since the product was a brown solution with precipitate it can be said that the potassium permanganate solution must have been slightly diluted with an alkaline.
  • 5. 4. Name the type of reaction that occurred in test tube C and write a balanced equation for the reaction. _______________________________________________________ _______________________________________________________ _______________________________________________________ The reaction was a combustion reaction. Equation for the reaction in test tube C. C2H4 (g) + 3O2 (g) 2CO2 (g) + 2H2O (g) Ethene undergoes combustion and forms carbon dioxide and water vapour. 5. Suggest some other substances other than aluminium oxide that could be used as a catalyst for the dehydration of ethanol. _______________________________________________________ _______________________________________________________ _______________________________________________________ Sulphuric acid and zeolites are commonly used as catalysts in the manufacture reaction of ethene from the dehydration of ethanol. Conclusion Write a suitable conclusion which incorporates the aim and your hypothesis. Ensure that a comparison is made to your hypothesis. ____________________________________________________________ ____________________________________________________________ ____________________________________________________________ ____________________________________________________________ Ethene was synthesized from the dehydration of ethanol and was then reacted with various reagents to undergo addition, oxidation and combustion reactions as hypothesized.
  • 6. Bibliography 1) Clark, Jim 2003, Oxidation of alcohols, viewed 1st of October 2010, <http://www.chemguide.co.uk/organicprops/alcohols/dehydration.html> 2) The Nuffield Foundation and Royal Society of Chemistry 2010, Dehydration of Ethanol to form ethene, viewed 1st of October 2010, <http://www.practicalchemistry.org/experiments/dehydration-of-ethanol-to- form-ethene,237,EX.html>