24.2Intramolecular hydrogen bonding between the hydroxyl group and the ester carbonyl can occur whenthese groups are ortho to each other.Intramolecular hydrogen bonds form at the expense of intermolecular ones, and intramolecularlyhydrogen-bonded phenols have lower boiling points than isomers in which only intermolecularhydrogen-bonding is possible.24.3(b)A cyano group withdraws electrons from the ring by resonance. Ap-cyano substituent is con-jugated directly with the negatively charged oxygen and stabilizes the anion more than doesan m-cyano substituent.p-Cyanophenol is slightly more acidic than m-cyanophenol, the Kavalues being 1.031028and 2.831029, respectively.(c)The electron-withdrawing inductive effect of the Fuorine substituent will be more pronouncedat the ortho position than at the para. o-±luorophenol (
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This note was uploaded on 10/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.