The phenoxide ion results from deprotonation of phenol and can be represented in…
CHEMISTRY · Multi-part · AP · Chemistry · Compound Structure and Properties · Compound Structure and Properties
Problem
The phenoxide ion results from deprotonation of phenol and can be represented in line-angle form as follows (text depiction): a six-membered benzene ring with alternating double bonds, one carbon of the ring bonded to an oxygen atom that bears a negative charge.
Respond fully to the prompts below.
(a) Draw one resonance contributor of the phenoxide ion in full Lewis form, including all lone pairs and formal charges.
(b) Systematically generate every distinct resonance structure that delocalizes the negative charge around the aromatic ring. Indicate the position of the negative charge in each contributor.
(c) Convert two of your resonance contributors into line-angle representations, making sure to denote heteroatoms and any required charges.
(d) Compare the delocalization of charge in phenoxide with that in the methoxide ion CH3O−. Using your resonance structures, explain why phenol is a stronger acid than methanol.