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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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?

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?
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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