Rank the following alcohols in decreasing order of acidity. Explain your answer.
A) II I III
B)I II III
C)I III II
D)III I II
E) III II I

Question

Rank the following alcohols in decreasing order of acidity. Explain your answer.  
A) II > I > III 
B)I > II > III 
C)I > III > II 
D)III > I > II 
E) III > II > I

Quizplus · Accepted Answer

The negative charge on the conjugate base of compound I is stabilized by three electron withdrawing fluorine atoms via inductive effect, making it the weakest base and the alcohol strongest acid.
The negative charge on the conjugate base of compound II is not stabilized, as it does not have any electronegative atoms on the carbon chain, making it a stronger base and the alcohol weakest acid.
The negative charge on the conjugate base of compound III is less stabilized than I, because it has only one fluorine atom connected. Thus making it a stronger acid than II, but a weaker acid than I.

Rank the Following Alcohols in Decreasing Order of Acidity