4. Acetic acid (pKa = 4.8) has two sulfur derivatives, thioacetic acid and dithioacetic acid. Thioacetic acid is about 100 times more acidic than acetic acid. Dithioacetic acid is predicted to have a pKa of about 2.1. Which of the three compounds is the most acidic? Offer an explanation using mechanistic reasoning. OH Acetic acid SH Thioacetic acid SH Dithioacetic acid

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4. Acetic acid (pKa = 4.8) has two sulfur derivatives, thioacetic acid and dithioacetic acid.
Thioacetic acid is about 100 times more acidic than acetic acid. Dithioacetic acid is
predicted to have a pKa of about 2.1. Which of the three compounds is the most acidic?
Offer an explanation using mechanistic reasoning.
OH
Acetic acid
SH
Thioacetic acid
SH
Dithioacetic acid
Transcribed Image Text:4. Acetic acid (pKa = 4.8) has two sulfur derivatives, thioacetic acid and dithioacetic acid. Thioacetic acid is about 100 times more acidic than acetic acid. Dithioacetic acid is predicted to have a pKa of about 2.1. Which of the three compounds is the most acidic? Offer an explanation using mechanistic reasoning. OH Acetic acid SH Thioacetic acid SH Dithioacetic acid
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