Constants of different acids and expressing the results as pK values, an acidity order can be established. Recall from section2.8 that a low pK corresponds to a strong acid and a high pK corresponds to a weak acid.
Where do hydrocarbons lie on the acidity scale? As the data in table 8.1 show, both methane (pK=60) and ethylene (pK=44) are very weak acids and thus do can de deprotonated by the conjugate by the conjugate base of any acid whose pK is greater than 25. Amide ion (NH-),for example ,the conjugate base of ammonia (pK=35) is often used to deprotonate terminal alkynes.
Why are terminal alkynes more acidic than alkenes or alkenes? In other words, why are acetylide anions more stable than vinylic or anions ? the simplest explanation involves the hybridization of the negatively charged carbon atom. An acetylide anion has an sp-hybridized carbon, so the negative charge resides in an orbital that has 50%”s character” a vinylic anion has an sp-hybridizded carbon with 33% s character, and an alkyl anion (sp) has only 25% s character. Because s orbital are nearer the positive nucleus and lower in energy than p orbitals, the negative charge is stabilized to a greater extent in an orbital with higher s character (figure8.5)