pKa Exercises Key

pKa Exercises Key - base having drastically different sizes...

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Chem 3A - Table of pKa's Exercises: Explain the differences between: 1 and 7 1, 7 and 10 8 and 10 11, 17, 19 and 20 2, 3, 4 and 9 6 and 16 6 and 12 12 and 18 16 and 18 14 and 15 13 and 15 1 and 7) The conjugate bases of 1 and 7 both have resonance stabilization; however the conjugate base of 1 is further stabilized by inductive effects. 1, 7 and 10) The conjugate base of 7 possesses more resonance stabilization (more resonance structures) than the conjugate base of 10 due to the higher valency of sulfur. 8 and 10) Same logic when comparing 1 and 7. 11, 17, 19 and 20) The difference in acidity between 17, 19 and 20 is based on the hybridized orbital that the lone pair occupies in the conjugate base. 17 is the most acidic of these three acids, because the lone pair is in a hybridized orbital with the greatest s character. 11 has the increased stabilization of the inductive effect compared to 17. 2, 3, 4 and 9) Differences in acidity are explained by the atoms in the conjugate
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Unformatted text preview: base having drastically different sizes. 6 and 16) Explained simply by the charge state of the acid. 6 and 12) The acid, 12, is more stable than the acid, 6, because the positive charge character is on a less electronegative atom (nitrogen vs. oxygen). Simply put, basicity decreases across a row of the periodic table (i.e., NH 3 vs. H 2 O). 12 and 18) Same reasoning as 6 and 16. 1 Chem 3A - Table of pKa's 16 and 18) The conjugate base of 16 is more stabilized in relation to the conjugate base of 18, because the negative charge is placed on a more electronegative atom. 14 and 15) The conjugate base of 14 has resonance stabilization, whereas the conjugate base of 15 does not. 13 and 15) The conjugate base of 13 places a negative charge on a larger atom, sulfur, than the conjugate base of 15. 2...
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