Which base would most effectively deprotonate benzoic acid (PhCOOH)? A)NaCl B)H₂O C)NaO₂CCH₃ D)t-BuOK E)All of these choices would effectively deprotonate benzoic acid.

Question

Quizplus · Accepted Answer

t-BuOK (t-butoxide potassium) is a strong base, and its steric hindrance allows it to selectively remove acidic protons in sterically unhindered positions. In benzoic acid, which has a relatively exposed hydrogen atom, t-BuOK would deprotonate it effectively. The other options either do not have sufficient basicity or lack steric hindrance to selectively remove the acidic proton in benzoic acid.

Which Base Would Most Effectively Deprotonate Benzoic Acid (PhCOOH)