Comparing Basicity: -OCH3, -OH, -NH2, and Alkyle with Negative Charge

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The discussion focuses on comparing the basicity of -OCH3, -OH, -NH2, and an alkyl group with a negative charge. It highlights that while -OH is a common base, its strength relative to the others is uncertain. The key point is that basicity can be assessed by checking the pKa of each conjugate acid, with higher pKa values indicating stronger bases. The provided pKa values show that NH2- is the strongest base among the options discussed. Overall, NH2- is identified as the strongest base due to its significantly higher pKa compared to the others.
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Homework Statement



-OCH3, -OH, -NH2, and the fourth choice is an alkyle, ethyne with a neg charge. the picture shows a triple bond attacked to a hydrogen.

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The Attempt at a Solution



I know that OH is a relatively common base and I thought it was strong, but I have no idea how it compares with the others. I know that alkyles are are less basic than alkenes and alkanes, but the oxygens throw me off a bit. I think that by having O in them it would suggest that their conj acid would be more acidic making them more basic. Is this correct at all? Is there an easy way to determine basicity?
 
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check the pKa of each conjugate acid. whichever has the highest pKa is the strongest base

water = 15.7
alcohols are between 16-18
NH3 is ~35
HCCH is ~25

so NH2- is the strongest base
 
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