Four organic compounds are listed below in no particular order.
1. Ethanol, CH3CH2OH
2. Phenol, C6H5OH
3. p-Cresol (4-methylphenol), CH3C6H4OH
4. p-Nitrophenol, O2NC6H4OH
Respond to the tasks that follow.
(a) Rank the four compounds from strongest acid (1) to weakest acid (4).
(b) For the compound you ranked as the strongest acid, draw all major resonance forms of its conjugate base.
(c) Justify the entire ranking in part (a) by comparing the relative stability of the conjugate bases and identifying the key electronic effects that account for any differences.