Question

question 36 of 47
for the list of alcohols, rank the alcohols in strength from weakest acid to strongest acid.
weakest
strongest
answer bank
f₃coh ch₃oh f₂choh fch₂oh

Explanation:

Acidity of alcohols depends on the stability of their conjugate bases (alkoxides). Electron-withdrawing fluorine atoms stabilize the negative charge on the alkoxide via inductive effect; more fluorine atoms or closer proximity to the -OH group increases this stabilization, making the alcohol more acidic.

1. $\text{CH}_3\text{OH}$ has no electron-withdrawing groups, so it is the weakest acid.
2. $\text{FCH}_2\text{OH}$ has one fluorine atom, providing weak inductive stabilization.
3. $\text{F}_2\text{CHOH}$ has two fluorine atoms, stronger inductive stabilization than $\text{FCH}_2\text{OH}$.
4. $\text{F}_3\text{COH}$ has three fluorine atoms, the strongest inductive stabilization, making it the strongest acid.

Answer:

Weakest → $\text{CH}_3\text{OH}$ → $\text{FCH}_2\text{OH}$ → $\text{F}_2\text{CHOH}$ → $\text{F}_3\text{COH}$ → Strongest