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Acidity of TMS Acetylene vs Methane

  1. Feb 1, 2017 #1
    1. The problem statement, all variables and given/known data
    Between trimethlysilylacetylene and methane, which is more acidic and why?

    2. Relevant equations
    No equations

    3. The attempt at a solution
    I believe the answer is trimethylsilylacetylene due to the location of the alpha proton being at the end of the alkynl group and with methane, all of the protons are equal and carbon will not readily give up any of the protons...am I correct?
  2. jcsd
  3. Feb 2, 2017 #2


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    Science Advisor
    Gold Member

    The right answer, but the reason is off. For example, both of the protons on water are equivalent, but water is far more acidic than either TMS acetylene or methane. What do you know about the bonding in alkynes versus alkanes?
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