Core Practical 5: The oxidation of ethanol

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9 Terms

1
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Overview:

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2
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Procedure:

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3
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Procedure:

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4
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N.B.

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5
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Write an ionic equation for the conversion of 1-bromobutane into butan-1-ol.

N.B. use structural formulae

CH3CH2CH2CH2Br (l) + OH- (aq) → CH3CH2CH2CH2OH (l) + Br-(aq)

6
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Draw a mechanism for the reaction and suggest why you have chosen this mechanism.

  • 1-bromobutane is a primary haloalkane therefore would react via the SN2 mechanism forming temporary bonds

<ul><li><p>1-bromobutane is a primary haloalkane therefore would react via the SN2 mechanism forming temporary bonds </p></li></ul><p></p>
7
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Describe the tests that will confirm (or otherwise) the presence of:

(i) butan-1-ol in the distillate

acidified potassium dichromate, changes from orange to green if alcohol is present

8
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Describe the tests that will confirm (or otherwise) the presence of:

(ii) unreacted bromoalkane

  • first add nitric acid to neutralise NaOH

  • add aqueous AgNO3

  • a cream ppt would form if bromoalkane was present

  • Ag+ + Br- → AgBr

9
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Analysis of the product shows that there is still unreacted 1-bromobutane present. What modifications could you make to the method to try and improve the conversion to butan-1-ol?

  • heat the reaction mixture under reflux for a longer period

  • use a higher concentration of NaOH at higher temperatures

  • use an excess of NaOH