Acidity of TMS Acetylene vs Methane

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SUMMARY

Trimethylsilylacetylene (TMS acetylene) is more acidic than methane due to the structural differences in their bonding. The alpha proton in TMS acetylene is located at the end of the alkyne group, allowing for greater acidity compared to methane, where all protons are equivalent and less likely to dissociate. The discussion highlights that while both TMS acetylene and methane have protons, the bonding characteristics in alkynes contribute to their acidity levels, contrasting with the behavior of alkanes.

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  • Understanding of acidity concepts in organic chemistry
  • Knowledge of alkyne and alkane structures
  • Familiarity with proton dissociation and bonding
  • Basic principles of organic functional groups
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Homework Statement


Between trimethlysilylacetylene and methane, which is more acidic and why?

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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?
 
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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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