Acidity of TMS Acetylene vs Methane

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In summary, trimethylsilylacetylene is more acidic than methane due to the location of the alpha proton at the end of the alkynl group. However, this is not the only factor determining acidity. The bonding in alkynes versus alkanes also plays a role, as seen in the higher acidity of water compared to TMS acetylene or methane.
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gspsaku
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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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  • #2
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?
 

1. What is the difference in acidity between TMS acetylene and methane?

The acidity of a compound is determined by its ability to donate a proton. In this case, TMS acetylene has a much higher acidity compared to methane. This is because the TMS (trimethylsilyl) group is a very strong electron-withdrawing group, making the hydrogen attached to the triple bond more acidic.

2. How is the acidity of TMS acetylene and methane measured?

The acidity of a compound can be measured using a technique called pKa determination. This involves measuring the equilibrium constant of the reaction between the compound and a strong base, such as sodium hydroxide. A lower pKa value indicates a stronger acid.

3. Why is the acidity of TMS acetylene important to study?

The acidity of TMS acetylene is important to study because it can have implications in various chemical reactions. For example, TMS acetylene can act as a strong acid catalyst in certain reactions, while methane is not acidic enough to serve as a catalyst. Understanding the acidity of these compounds can help in designing more efficient and selective reactions.

4. Can the acidity of TMS acetylene and methane be altered?

Yes, the acidity of these compounds can be altered by introducing different functional groups. For example, adding a stronger electron-withdrawing group to TMS acetylene can increase its acidity even further. Acidity can also be affected by the solvent and temperature of the reaction.

5. How does the acidity of TMS acetylene and methane affect their reactivity?

The higher acidity of TMS acetylene makes it a more reactive compound compared to methane. This is because the acidic proton in TMS acetylene can be easily abstracted by a base, leading to the formation of a more stable intermediate. This increased reactivity can result in different products being formed in reactions involving TMS acetylene and methane.

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