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Ch.21 - Organic Chemistry

Chapter 21, Problem 104

The hydrogen at C-1 of 1-butyne is much more acidic than the one at C-1 in 1-butene. Explain.

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Hello everyone today we are being asked to identify the statement that best describes why the hydrogen and methane are more acidic than the hydrogen and methane. So the correct answer is going to be be because the thin has a higher percent of S. Character than anything, recall that the higher S. Character is generally tied to a stable conjugate base for C. B. So when we do protein eight, a single hydrogen from these structures we leave behind a pair of lone pairs. And so for a thin it's going to be sp hybridized. That means that it's going to be 50% s. and 50% p. character. So that's going to have a higher S. Character compared to ethane Which will be s. p. two. And that will be about 33%. So it's going to have less s. character Going back to 18. The higher the s. character. You're going to have more stability of that conjugate base and therefore you're going to have a more acidic structure. So that's why B. Is correct. I hope this helped. And until next time.