Arrange the following molecules in order of increasing pKa:

CH₃CH₂COOH, CH₃CHFCOOH, CH₃OCH₂COOH, CH₃CHBrCOOH

A) CH₃CHFCOOH, CH₃OCH₂COOH, CH₃CHBrCOOH, CH₃CH₂COOH

B) CH₃CHBrCOOH, CH₃OCH₂COOH, CH₃CH₂COOH, CH₃CHFCOOH

C) CH₃CHFCOOH, CH₃CH₂COOH, CH₃CHBrCOOH, CH₃OCH₂COOH

D) CH₃CH₂COOH, CH₃OCH₂COOH, CH₃CHFCOOH, CH₃CHBrCOOH

Explanation

Increasing pKa means decreasing acid strength. A low pKa, just like a low pH, indicates a stronger acid. Here, we need to arrange the molecules from the strongest acid to the weakest.

An acid is stronger if the conjugate base is stabilized, and one form of stabilization is inductive stabilization. That is, if an electron withdrawing group pulls electron density off of a carbon, that carbon becomes slightly positive. That slight positive charge can then stabilize the negative charge of the conjugate base.

Inductive effects increase with increasing electronegativity. Because fluorine is the most electronegative atom, it has the biggest inductive effect and will most help stabilize the conjugate acid. Thus CH₃CHFCOOH is the strongest acid and must be first in our list. That narrows us down to (A) and (C).

Propanoic acid with no inductive stabilization would be the weakest acid here, with the highest pKa. So it must be the last item on the list. That tells us choice (A) is the right answer.

Want more MCAT practice?

We’ve got options for every schedule and learning style!

From the best online MCAT course created by top instructors with 524+ MCAT scores to the most representative full-length practice exams and private tutoring, we can custom tailor your MCAT prep to your goals!

Not sure which option is right for you? Schedule a free MCAT consultation with an MCAT expert using the form below. No obligation, just expert advice.