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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.
Structural formulas of ethyne and ethene, illustrating differences in functional groups.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Acidity and pKa

Acidity in organic chemistry refers to the tendency of a compound to donate a proton (H+). The strength of an acid is often measured by its pKa value; lower pKa values indicate stronger acids. In the case of 1-butyne and 1-butene, the hydrogen at C-1 in 1-butyne is more acidic due to the stability of the resulting anion after deprotonation, which is influenced by the hybridization of the carbon atom.
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Hybridization

Hybridization is the concept of mixing atomic orbitals to form new hybrid orbitals that can accommodate bonding. In 1-butyne, the C-1 carbon is sp-hybridized, while in 1-butene, it is sp2-hybridized. The sp-hybridized carbon has a higher s-character (50%) compared to sp2 (33%), which means the electrons are held closer to the nucleus, making the hydrogen more acidic in 1-butyne.
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Resonance Stabilization

Resonance stabilization occurs when a molecule can be represented by two or more valid Lewis structures, leading to a more stable overall structure. In the case of the anion formed from deprotonating 1-butyne, resonance can stabilize the negative charge, enhancing the acidity of the hydrogen at C-1. In contrast, the anion from 1-butene lacks similar resonance stabilization, making it less acidic.
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