16. (a) Predict which proton in ascorbic acid (vitamin C) would be the most acidic. Explain using the stability of the conjugate base produced by removing each proton. НО. HO HO OH

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(c)
CH3CO₂O, CH3CH₂00, BrCH₂CO₂0
16. (a) Predict which proton in ascorbic acid (vitamin C) would be the most acidic. Explain using
the stability of the conjugate base produced by removing each proton.
HO-
HO
HO
HO
(b) Explain why ascorbic acid is slightly more acidic than acetic acid (CH3CO₂H).
OH
17. Predict which analgesic, acetaminophen or aspirin is more acidic. Explain.
LOCOCH 3
Acetaminophen (Tylenol)
LOH
Acetylsalicylic acid (Aspirin)
piwollot ori ins
10 HO HOD (6)
Prior Kr
Before b
Learn
Cont
Afte
Pr
Transcribed Image Text:(c) CH3CO₂O, CH3CH₂00, BrCH₂CO₂0 16. (a) Predict which proton in ascorbic acid (vitamin C) would be the most acidic. Explain using the stability of the conjugate base produced by removing each proton. HO- HO HO HO (b) Explain why ascorbic acid is slightly more acidic than acetic acid (CH3CO₂H). OH 17. Predict which analgesic, acetaminophen or aspirin is more acidic. Explain. LOCOCH 3 Acetaminophen (Tylenol) LOH Acetylsalicylic acid (Aspirin) piwollot ori ins 10 HO HOD (6) Prior Kr Before b Learn Cont Afte Pr
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The acidic strength of a proton can be determined in terms of the stability of the conjugate base. The conjugate base is the molecule obtained by removing the acidic proton. The more the resonating structures for a conjugate base, more will be the stability and more will be the acidic character of that proton. Most acidic protons are the ones whose conjugate bases have highly resonance stabilized.

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