Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 8.7, Problem DQ

The strength of the H─O bond in vitamin E is weaker than the C─H from which the hydrogen is abstracted in the fatty acid primarily because,

  1. 1. O─H bonds are always weaker than C─H bonds.
  2. 2. The radical created from hydrogen abstraction from O─H is stabilized by resonance delocalization and many of the contributing structures have secondary carbon radical character.
  3. 3. The sp2 hybridization of the phenyl ring changes the hybridization of the oxygen in the O─H bond.
  4. 4. The radical created from hydrogen abstraction from O─H is stabilized by resonance delocalization and many of the contributing structures have tertiary carbon radical character.
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