3. Acids and Bases

Identify the most stable conjugate base in each pair. Tell which structural features you analyzed and why you weighted them as you did in picking one answer.

(c)

Identify the most stable conjugate base in each pair. Tell which structural features you analyzed and why you weighted them as you did in picking one answer.

(e)

Identify the most acidic proton in each pair. Tell which structural features you analyzed and why you weighted them as you did in picking one answer. [Always start by drawing the conjugate base.]

(a)

Identify the most acidic proton in each pair. Tell which structural features you analyzed and why you weighted them as you did in picking one answer. [Always start by drawing the conjugate base.]

(h)

Which anion in each pair would you expect to react more quickly with H⁺?

(a)

Which anion in each pair would you expect to react more quickly with H⁺?

(b)

If reacted with a strong base, which of the labeled protons would you expect to be removed first?

Which is the most acidic compound in each pair?

(a)

Rank the indicated hydrogen in the following compounds from most acidic to least acidic:

Which member of each pair is the stronger base?

c. phenolate ion or ethoxide ion

d. phenolate ion or acetate ion

Which member of each pair is the stronger base?

a. ethylamine or aniline

b. ethylamine or ethoxide ion

Which acid in each of the following pairs is stronger?

e.

f.

Purine is a heterocyclic compound with four nitrogen atoms.

a. Which nitrogen is most apt to be protonated?

b. Which nitrogen is least apt to be protonated?

Which acid in each of the following pairs is stronger?

c.

d.

For each of the following substituents, indicate whether it withdraws electrons inductively, donates electrons by hyperconjugation, withdraws electrons by resonance, or donates electrons by resonance.

d. NHCH₃

e. OCH₃

f. ⁺N(CH₃)₃