Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the correct order of increasing acidity for the following compounds.
Correct answer
3
Step-by-step solution
The acidity of a compound is directly proportional to the stability of its conjugate base. For cyclohexanol, the conjugate base (cyclohexanoxide ion) is not resonance stabilized and is destabilized by the +I effect of the cyclohexyl ring. For phenol, the conjugate base (phenoxide ion) is stabilized by resonance delocalization of the negative charge over the benzene ring, making it more acidic than cyclohexanol. For p-nitrophenol, the conjugate base is further stabilized by the strong electron-withdrawing -R and -I