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will ammonia deprotonate ethylene? |
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yup. ammonia pKa 33, ethylene pKa 25
it's the amide ions that will deprotonate the ethylene, not ammonia itself |
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pKas of:
ethane,
ethene,
ethylene |
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[image] , [image], [image]
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15.9, 4.8, -1.9
The trend is due to the fact that the respective conjugate bases get more stable for compounds left to right bc of nr of O atoms. pretty cool |
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why does ethane has higher pKa than ethene? |
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Upon the removal of H from ethane, the e will stay in an sp3 orbital, which is less stable than an sp2 orbital resulting from deprotonation of ethene. |
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Are e in sp or sp2 orbitals lower in energy? |
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sp, because an sp orbital has more s character than an sp2 orbital. An s orbital is more stable bc s orbitals are closer to the nucleus and very low in energy |
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