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[6] Determining acidity using hybridization effects (2.5D)

[1] Draw the conjugate bases of the follow- [2] Identify the hybridization of the [3] Determine the
ing compounds. carbanions. stronger acid.

• The higher the percent • The acidity of

s-character of the hybrid HA increases as
orbital, the more stable the percent s-
the conjugate base. character of A: -
increases.

See Figure 2.5. Try Problems 2.51d, 2.54d.

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[7] Determining the most acidic proton (2.5E)

[1] Identify the atoms bonded [2] Draw conjugate bases and resonance [3] Determine most acidic
to hydrogen, and use structures. proton
periodic trends to assign
acidity.

• The oxygen anion stabilizes the

conjugate base through resonance
unlike the nitrogen anion. Hence,
the hydrogen atom bound to the
oxygen atom is more acidic.

• If two H atoms in question are

bonded to the same element, draw
• HOR is more acidic than the conjugate bases and look for
H2NR based on other differences:
electronegativity. 1) Do electron-withdrawing
groups stabilize the conjugate
base? If yes, the stronger the acid.
2) Is the conjugate base resonance
stabilized? If yes, the stronger the
acid.
3) How is the conjugate base
hybridized? sp3 has 25% s-
character, sp2 has 33% s-
character, and sp has 50% s-
character; the more s-character,
the more stable the conjugate base
and, therefore, the stronger the
acid

See How To (p. 76), Figure 2.6, Sample Problems 2.7, 2.8. Try Problems 2.43, 2.44, 2.52, 2.64.