
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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I understand that the diradical dioxygen attacks a hydrogen on the carbon adjacent to the double bond but can I be shown the resonance mechanism and why we can't use a hydrogen directly from the double bond?

Transcribed Image Text:Triglycerides (which make up cooking oils) tend to become
rancid with time as they react with oxygen. This occurs
because the triglyceride molecule reacts with oxygen to form
carbon-centered radicals, which can create a chain reaction
resulting in chemical cross-links between lipid chains. Oxygen
(02) can exist as a diradical species and can do a hydrogen
abstraction reaction. R represents the rest of the triglyceride
OR
oleic acid
OR
linoleic acid
structure.
Draw the Lewis structure for dioxygen (0,) and draw a resonance structure of dioxygen in its diradical form:
Draw a hydrogen abstraction reaction of diradical oxygen with oleic acid (a monounsaturated fatty acid).
Which hydrogen(s) is(are) most easily abstracted? Why?
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