Dolbier HW Solutions 583

Dolbier HW Solutions 583 - 677 PHENOLS 24.2 Intramolecular...

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24.2 Intramolecular hydrogen bonding between the hydroxyl group and the ester carbonyl can occur when these groups are ortho to each other. Intramolecular hydrogen bonds form at the expense of intermolecular ones, and intramolecularly hydrogen-bonded phenols have lower boiling points than isomers in which only intermolecular hydrogen-bonding is possible. 24.3 ( b ) A cyano group withdraws electrons from the ring by resonance. A p -cyano substituent is con- jugated directly with the negatively charged oxygen and stabilizes the anion more than does an m -cyano substituent. p -Cyanophenol is slightly more acidic than m -cyanophenol, the K a values being 1.0 3 10 2 8 and 2.8 3 10 2 9 , respectively. ( c ) The electron-withdrawing inductive effect of the Fuorine substituent will be more pronounced at 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.

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